Housing- you'd have to ask at the specific school you're applying to. I went to a vocational school and there was no campus housing, BUT there were local residents willing to rent rooms in their houses, to students attending the truck driving school. I believe I paid $70 a week for a room, bathroom and full use of the kitchen, and I went home on the weekends.
Some schools have limited housing, some have the same scenario I mentioned. You could also look into companies that offer free driver training....they usually provide housing and meals while you are in training. The drawback is you are required to stay with them for usually 1 year, and if you quit, you owe them money.
If you're looking at a state-funded community college or vo-tech, there should be grants and financial aid available. Ask about it at the school. "Trucking schools" that operate as for-profit businesses usually have loan programs that you pay back after you are employed.
Tuition reimbursement- you go to school first, then get the job. Read the fine print, most companies offer "tuition reimbursement" but it's paid out in $250 dollar increments, every 3 months, over the next 3 years or something like that.
Company driver vs. owner/operator.....definitely go with being a regular company driver for a while. Learn the industry. Decide whether it's what you REALLY want. Being an owner operator requires a huge level of financial commitment & responsibility....and with low freight rates and high fuel prices it is getting harder and harder to "make it" as an owner/op. You've really got to know the industry if you're going to do well as an owner operator.
Average pay for an average company driver is 35,000-55,000 a year. However, as you gain experience there are opportunities to "specialize" in various types of freight....hauling cars, oversized loads, concert and stage equipment for singers, etc....pays very well and you're still a company driver.
There are also linehaul (regional) opportunities available with companies like FedEx, UPS, Saia, R&L Carriers, Estes, etc...some of these companies pay upwards of 70,000 a year. Grocery store delivery drivers are usually home nightly and many of them are union, the jobs often pay quite well. Jobs with Wal-Mart will have you home at least every other night (or you can customize your schedule) and I heard 'through the grapevine' they pay their drivers about 78,000 a year. So you can definitely make a nice living without being an owner/operator, just stay safe and keep a good work history.
Taking the truck home- most OTR companies will allow you to take your truck home when you go on home time. Most companies won't even notice if you use the truck a couple of times to run a short errand here or there, but they don't permit you to use it as your "personal vehicle" to run all around town.
If you don't have a car right now, when you initially get hired with a company, they will usually pay for your bus or plane ticket to come to their terminal for orientation. This is where you will be assigned a truck, and from that point on, it goes where you go.