So tying this all together, would this persistent world of sorts bother you? Let's say it is not forced, and customers can be generated in your own little world, but if you 'connect' you have access to not only viewing other people's creations and work, but being a part of a 'living and breathing' world of customers who simply want to have a good time and have different needs.
Would there be a geographical element to the game? (travelling, etc.)
In this vein, I would imagine that two competing similar businesses could exist if only because a portion of the users wouldn't bother going the distance to the "best" of these places and settle for the closest one... this is a decision a lot of us do on a daily basis
Is this a problem of perhaps I'm worried players will become bored waiting for games to end? Do you think this can be avoided by giving the players enough to do other than simply working on the courts, then watching players for ever and ever play on them? What if they have a 'perfect' business? Would you simply watch the games and earn money so that you could spend it on, well, nothing besides perhaps some internet fame (or building another 'location') for procuring 10000 professional players in your corporation's life time?
We still watch football don't we? Besides, I've seen fully asynchronous games where you get to play "a turn" once per week, and they still do good.
If your concept is sound, and if you have a subset of users in mind, some will survive these limitations for sure...
If you can make the outcome of matches played uncertain, keep a level of competition, and make it very hard to break ahead, games will remain fun to watch, and will provide entertainment while money comes in.
For the rest of the post, I'm affraid that you've been very unclear about the exact nature of your concept, perhaps because even some of it remains unclear to you. I don't come out of this lenghty reading with a precise understanding of what you're trying to achieve, which makes it hard for me to comment efficiently on your questions...
My appreciation is that you're currently having "coldfeet" and not making the decisions you should be making. Merging two gameplays? sure. Scare of losing playerbase as a result? there's actually no avoiding this, and if you try to please everyone, your game will suck for everyone. Decide on a persona, a subset of users, and stick to that plan, rather than try to pick up on large ensembles such as casual and simulation players.
Pick "Jonnhy", the guy that works at a software company 50h/week, two kids, a wife, has a 10 years old car parked in the garage, and earn approx 40k$/year. This guys doesn't have much time, but he wants to make the most out of it, but he wants to appreciate his time, so he's probably not going to try min/max your game. If you provide him with a clever experience with some self-expression, he might just as well jump in.
Why this persona? (you could definitely build another). Over the last couple of years, we've focused so much on Soccer-mums, that I don't think soccer-mums have anymore time left to play games. They're so busy on Farmville they can't even raise their kids. Might as well focus on somewhat busy adults with limited gaming time and build an experience suited for them. These guys are having a rough time following up with the amount of time it takes to play games like WoW, and always being far behind.