OK here are a few things.
First I feel that it takes 2 years of more to really learn the business. I mean that you may learn a lot in your first year to make money but don’t expect that to be it, you are always learning and the real money comes after that time. A few here will say that you can learn everything in a month or two, not true. And Remember that this is like the IT business, there is no such thing as an expert.
Second you got to treat this as a business, because that is what it is. You are a service provider, not a truck driver (yea I know there will be disagreements with this one) so understand that the customer makes this all possible and making it look like (and actually) caring about the service to them sometimes makes a big difference. Also with that in mind, get your financial house in order, some say it is not really a big deal but start with getting advice (i.e. an accountant and a lawyer lined up) and start thinking about goals to document in your business plan.
Third, to answer your questions;
Yes you can make money running solo, but it depends on the goals you set. Being realistic unless you have owned a truck before and ran it, maybe a newer truck is in order but if you never have done this before, look to buy a used truck, something entry level and with no frills. This will allow you to keep overhead low and you can save up for a bigger (maybe a new) truck in a year.
Yes the Midwest I very good and so is the south east. I like the south myself right now, maybe because I don’t like the cold (and I can’t figure out why I came back to Indy?). Remember that this is a customer dependent business and has cycles. For example, Atlanta may be booming for several weeks and the next month it may be slow while St Louis is booming, so think about keeping track of the good areas you are successful in a note book with dates – a little analyzing may go a long way but don’t fall into the trap of thinking that you can figure out trends in this business, if one can they would be millionaires over night.
Hope this helps.