I almost exclusively sell bank foreclosures for a large asset management company, and I also do a lot of marketing for wholesale deals.

Best thing to do is start by reading The Ultimate Guide to Grading Cleveland Neighborhoods.

We are Canadians eyeing up the market in the USA and looking to start investing in properties across the border. 

Cant speak for Nashville, but nationally Redfin recently released a report on their own transactions (they can see both sides of it) that average commissions have risen.This is no surprise to me as I predicted this would happen far in advance of the settlement.

With your budget, depending on where you are working, I'd consider Silver Spring or Hyattsville  

Going to do another? 

I have been reading the online resources about getting started, searching the market, and even doing tours, but I am hesitant to jump in and buy a house as I have quite a large amount of student debt.

Scott as a starting reference.

Even give them a call to ask about wholesaling as a broker.That'll get your education started off right!

I highly recommend going to meetups and talking to investors in person.