I know that if your company rating is too low they say something like "your company is not big enough for me." I know that wrestlers will refuse to negotiate if you have previously fired them or if they are happy with their current company (or if you're rating is too low for them). I might be able to provide a better answer knowing more specifics. Otherwise, have you posted this over at their message board?
Has anyone else here had a problem in the new update where they buy out a company where you're supposed to get all the contracts, the game crashes, when you come back the company still exists and all their old talent are now free agents, and you're out the cash you spent to buy the company in the first place?
You never know when you'll meet that special someone... the someone that's mysteriously blind to your flaws. or, you know, stupid enough not to realize that yes, you really are that cynical.
That hasn't happened to me, but I haven't tried to buy anyone out. I did hear about that happening to other people over at the EWR site, and Adam either fixed it in the most recent patch, or else the fix is upcoming. Check the site.
Skip the Interstates when you hit Chicago. Take Lake Shore Drive (US-41.) You'll lose time but the trip through downtown Chicago (still at decent speeds...well, depending on the time of day) is immaculate. Navy Pier! Soldier Field!