Local knowledge can be vital, and vaguely similarly described comps can be very misleading when trying to establish what a particular property is REALLY worth.How much capital expenditure will be soon required in order to keep it habitable?

My first suggestion is to establish a goal, do you want to have a turn-key to obtain your passive income?  

From an outsider's perspective I'd say that you should keep your 9-5 for a while longer while you get established as an agent.

An area that's already established or one that is on the rise? 

Absolutely, there are a bunch of real estate plays that don't require much money or good credit:Become a lead finder ("bird dog") for a well-established investor or wholesaler in your area.

Hello @Scott Schaeffer in BP.I'm not a legal or tax advisor, however based on my experience, the savvy investors usually establish an LLC partnership with a 2% member that is also an LLC taxed as a C-corp.

No simple answer but establish your criteria price, profit, location/s, time per project, level of rehab, property type, etc.

Well, I just know a lot of people in my area and I know an actual brick and mortar presence would probably help me out in establishing myself quicker.

Establish an "unauthorized occupant" clause, with a hefty fee for violating this, in your lease/rental agreement.

@Max Tanenbaum has great advice. an established roofing company may be to let you differ payment, which would be like financing with no interest involved. they get the business, and with a signed contract can spread their payment out over the winter, when their business slows down