Also I'm not sure yet what kind of closing costs and or fees this lender will charge for this deal yet.

This is probably kind of ridiculous to ask for such a favor, I just don't know who to ask I don't know anyone that has a clue.

I kind of think I should be looking more along the 5plex over single family from my research so far?

I'd love to hear your thoughts on what kind of mail typically works best (typed letter, handwritten yellow letter, postcard, etc.), how can I quantify the amount of repairs the house is going to require (I have an idea of the ARV by looking at comps in the area, but I wouldn't know what to offer because I haven't seen the inside of the house and don't know the repairs required), and any other advice that you may have.

You'll also want to have some kind of document for the tenants to sign that more or less says "the lease is over and I'm moving out."

But the kind of tenant who will let things go all the way to eviction court, probably doesn't care about that. 

I think a common standard is 30,000 persona l property/100,000 liability, and is what I require in new leases.

The common area things they provide and their looks of the entryway provided will also help you know what to look for when purchasing.It's location is very important as well as its access. 

My buddy has all kind of contractors and repairmen in the Memphis area.

I know a couple guys in my home town that served 5+ years in a federal prison for this.If you're moving ownership into a land trust that you also control and have no intention of defaulting or selling and avoiding the payoff, it could for sure be argued as positive fraud, but the intent would more likely be for something like asset protection or some kind of investment arbitrage - which could still be fraud.