This is an interesting topic to me and brings to mind an idea of mine which... will never be implemented because the industry is going in a completely opposite direction (honestly it could be a terrible idea that I haven't thought through enough anyway). I probably won't have space to add that here. Nevermind, off topic.

To give my take on an answer to the OP - as usual it's heavily dependent on requirements (damn those things!). IMO you (in the general sense) need to examine the topic from both an "Internet" perspective and an "enterprise/business" perspective. I could probably write a small book on the subject (sad, really) and I was starting to respond with what looked like a first chapter before I came to my senses. Many people seem to focus only on the Internet side (which is more visible than internal business intranet stuff) and so I think many managers and developers end up following the Internet's lead, but a business intranet has some important differences. What works best for the Internet may not be the best solution for a private intranet.

What do you mean by "they live on the server"? By thinking that way, you could argue for changing almost anything that touches a database into a webapp. I'm unclear regarding what advantages you perceive would be gained from a conversion to a web application. But in my opinion webapps are definitely more complicated and usually more work intensive (usually still Java based anyway, in a business setting). In a business environment, I can't justify using them for a tiny user base (if that's the case).

Since the main pro (no installs/updates) is well known, I'll throw out some of the cons for a small web-based data-centric/business intranet reporting application with a small user base (alter part of that and this list can change dramatically) which your manager may be thinking of. Also, I'm having a hard time thinking of other pros with the information you provided.

-Additional development complexity. More scaffolding, more libraries/frameworks, dependencies, tools, concurrency considerations, sessions, knowledge and so on are required...you probably know this, but I don't take this one lightly. Complexity level vs. a Java thick client isn't even close, IMO.

-More complicated server side to deal with. Depending on environment complexity and factors like whether you have a pack of security goons nagging you, this can get bad.

-Harder (and often slower) to debug web-based stuff

-Net connection required, no "disconnected mode" (this may be a moot point with a reporting application if there's a remote database involved)

-Loss of easy access to useful local functionality such as the operating system clipboard, disk storage (without having to bother with cookies and such), screen captures, etc.

-DHTML still sucks. CSS & DOM are the 800lb gorillas in the room and they're still not pretty. The more browsers you're coding for, the worse it gets. But this may not matter in your environment if you're standardized to one browser. Dev frameworks make this easier but they still need to be updated to keep up with the browser mess.

-Not sure what tools you have available, but relatively speaking, web dev front end tools generally aren't much fun to use - assuming your tech of choice even has one.

On the other hand, a Java (Swing I assume) application for a small number of users to do some reporting - I can think of some nice advantages here. Swing isn't perfect but it can get much worse. If you're having layout manager problems I'd suggest dumping that crap, use a null (absolute) layout and a decent UI builder tool for a complex UI. You don't need to worry about resizing stuff for 50 different sized screens, do you? (Even then you could use null layouts in smaller parts.)

To give a better analysis of "who has the better argument" we'd have to have more requirements, such as the size of the user base, size of the application, what type of reports it's generating (graphics, tabular, etc), amount of data being processed & displayed, how many controls need to fit onto a screen, what technology/tool options are available etc.

It sounds like your manager might have some dev experience, which could mean that he knows what he's talking about... or he has some bias.

It sounds like you are having interface design problems.

It does, and if so I'd bet that a layout manager is giving him fits.

You have to consider the all the requirements --

If the program needs a connection to the network to do anything useful (e.g. it queries a database or reads/writes other network resources) then you need to have network connectivity one way or the other. On the other hand, if you can do useful stuff without a network connection, then a program that can be deployed on a workstation won't be brought down by a network outage.

How much processing power does the application need? Are you better off spreading that out among each user's workstations, or do you have a big enough on-premises server to handle the number of concurrent users you expect? All possible users? 3x that, if the company grows? Does the application scale up, or does it scale out?

What are the things you could do if the app lived on a server that would be difficult to do in an app? Collaboration? Continuous analytics? real-time analytics?

Modern web applications can be very, very robust and capable. Google has google docs, Microsoft has a very feature-rich IDE in beta. The web has come a long, long way since forms and post-backs. There's effectively nothing you can't do in a browser today, as long as you're happy playing in the sandbox that browsers give you.

The general benefits of running an app on a server are that you have control of the environment to a greater degree, and you don't have the (potential) headache of deploying and maintaining the app across a large number of workstations. This can have fringe benefits like being able to roll out new features and bug-fixes rapidly and incrementally (obviously, well-tested first), something that's too costly to consider when 10s or hundreds of workstations need to be kept in sync.

You may have to tow the party line, but it sounds as if your boss is very old-guard, and might be concerned that a changing world will leave him out of a job. He might not be up on the state of web development, or perhaps he is, but knows he doesn't have the expertise on staff to make the transition in a cost-effective way, or quickly enough to meet milestones. There are countless good or bad reasons to not do something, even if that something really is a great solution.

-Additional development complexity. More scaffolding, more libraries/frameworks, dependencies, tools, concurrency considerations, sessions, knowledge and so on are required...you probably know this, but I don't take this one lightly. Complexity level vs. a Java thick client isn't even close, IMO.
-More complicated server side to deal with. Depending on environment complexity and factors like whether you have a pack of security goons nagging you, this can get bad.
-Harder (and often slower) to debug web-based stuff
-Net connection required, no "disconnected mode" (this may be a moot point with a reporting application if there's a remote database involved)
-Loss of easy access to useful local functionality such as the operating system clipboard, disk storage (without having to bother with cookies and such), screen captures, etc.
-DHTML still sucks. CSS & DOM are the 800lb gorillas in the room and they're still not pretty. The more browsers you're coding for, the worse it gets. But this may not matter in your environment if you're standardized to one browser. Dev frameworks make this easier but they still need to be updated to keep up with the browser mess.
-Not sure what tools you have available, but relatively speaking, web dev front end tools generally aren't much fun to use - assuming your tech of choice even has one.

To be fair though, most of those that seem most hairy are not inherent problems in the platform, but a question of having people with the right know-how. From a business perspective, absolutely what resources and skills you have to carry out an implementation matters -- it probably matters more than just about any other factor -- but lets not be confused that they are insurmountable. I don't think you meant to imply as such, but what you said might read that way to someone less versed in these matters.

Also, if this is an app meant to run within an enterprise, then many of the real (but likewise not insurmountable) issues with browser-compatibility or feature-set melt away. Many people will decry web-apps as a total no-go due to the problems that arise from the variety of browsers you would have to support to deliver on the promise of "runs anywhere" -- To that I say, loudly, "So What?" -- Pick a browser, any browser, that supports the features you need and declare it as your supported browser. On a corporate network, the powers that be absolutely can make it so. Even in the Internet Frontier, 300 million people have a modern chrome browser installed, that's a pretty damn good install base by any measure.

It does, and if so I'd bet that a layout manager is giving him fits.

No, it's not a layout thing. I've been using Miglayout for years. It isn't a question of knowing how to layout the GUI, from a technical standpoint. I've made dozens of Java GUIs over the years.

It's that the application is looking like that. Which I don't like.

It's that the application is looking like that. Which I don't like.

Oh god, that is painfully close to the bone

It's that the application is looking like that. Which I don't like.

This is what UX (that is "user experience", for the uninitiated) designers are paid the big bucks for.

(well, maybe not so big. But paid, at least)

Since I have to assume that you don't have any UX resources assigned to this project, you probably need to learn to think like one. Build a list of the features you are adding. For each feature, whiteboard/flowchart the steps the user should go through to complete the task. Factor out common sub-tasks if there is significant overlap between the steps required to use a set of features. Implement each distinct feature as a single continuous flow (don't try and cram all features into a single screen, don't provide options on a given screen which are irrelevant to the current task). Read a copy of the design of everyday things. Profit.

It's that the application is looking like that. Which I don't like.

This is what UX (that is "user experience", for the uninitiated) designers are paid the big bucks for.

(well, maybe not so big. But paid, at least)

Since I have to assume that you don't have any UX resources assigned to this project, you probably need to learn to think like one. Build a list of the features you are adding. For each feature, whiteboard/flowchart the steps the user should go through to complete the task. Factor out common sub-tasks if there is significant overlap between the steps required to use a set of features. Implement each distinct feature as a single continuous flow (don't try and cram all features into a single screen, don't provide options on a given screen which are irrelevant to the current task). Read a copy of the design of everyday things. Profit.

Yes, this sounds like what is happening. I've never heard of this book, but I cant wait to check it out.

It does, and if so I'd bet that a layout manager is giving him fits.

No, it's not a layout thing. I've been using Miglayout for years. It isn't a question of knowing how to layout the GUI, from a technical standpoint. I've made dozens of Java GUIs over the years.

It's that the application is looking like that. Which I don't like.

Hey, you stole our application design theme... so yeah, you're definitely having design troubles, not tech with that level of experience.

But seriously, I don't know if your users fall into this category or not, but ours actually ask for this type of interface more often than not. I just re-designed an application specifically to consolidate screens (although, I must say it's quite a bit prettier than the comic example). I've been in your exact situation - sometimes we're asked to pack so much into a small space (oh, and it has to look nice too) that it takes days just to come up with an initial prototype, which gets revised 5 times. I find that visual breaks and logical groupings help quite a bit (i.e. TitledBorder and so on I believe it's called in Swing).

But if the users are happy, I tend to just go with that unless I think they're sabotaging themselves. IMO the difference with these data heavy apps and a Google/Apple app is that one is designed for maximum productivity/speed, and the other is designed for ease of use and attractiveness. Two very different sets of requirements! I doubt an Apple or Google can completely solve such a problem, and if they did, I'd bet that productivity is taking a big hit. Maybe I'm just ignorant but I'd say most of the time there's a reason all these apps look busy.

If you really just want to switch tech, you could try a rich client SDK on your manager like Apache Flex or JavaFX to see how he reacts to that. But I imagine it'd be hard to justify replacing something that already is working. Choose your sales pitch wisely... lol