I don't think you realize just how much things change within six months, much less 2-3 years from now. Even if you're doing your research the right way, you may not be able to tell which company will be the best for you until just a few months before you're ready to apply. Time to the left seat at Eagle right now is still among the longest in the regional industry, but a lot might change by the time you're ready. It's good that you're asking questions, but at this point you need to be much less concerned about QOL, upgrade, and domiciles and just worry about getting your training in. Assuming it will take you at least a year to get all your certs, three years is an eternity in this industry.

Two years before starting training is also a long time in the flight school industry. Since you want to use your GI Bill, you have to go to a part 141 school with a VA-approved program. You cannot train under part 61 and get VA reimbursement. Right now, many of those larger 141 schools are changing policies and enrollment options to accommodate foreign training contracts, rather than U.S.-based students or veterans. U.S. students find it harder to find the financing compared to Chinese or Indian students, and that's where the money is. I know of at least two major flight schools in Arizona who have stopped accepting U.S. students all together and get 100% of their business through foreign contracts. Many 141 schools are going that direction to stay afloat. Also, since the GI Bill doesn't pay a dime toward your Private license, you should just find a seasoned instructor at a small local airport for your first license. It will be cheaper, and probably better instruction than many of the 141 pilot factories out there.