Going forward, I would like to create different LLCs for my properties to help mitigate the risk but don't know if this is an industry norm in the residential world. 

I have been looking into non-performing notes and while higher risk, I believe they may be a better start.

You're going to have carrying cost and this is a far cry from a seller rent back scenario.

Surely his first response is don’t do it but it’s all about the numbers and risk (and thus 2nd house) May be to risky with unknowns on lien and eviction.  

After speaking with two attorneys, they strongly recommended I didn't forego using an attorney and one even said I could be at risk for practicing law without a license.

Thinking about how to minimize risk on current residence, while maximizing its appreciation to purchase a rental property... 

I am going to start the process of wholesaling, I would like some guidance on how to start and to make this calculated risk work.

If he does so, offer to give him a good reference.I cant imagine talking to a lawyer over 50 bucks.. just take the check.. write them a nice letter and tell them that the late fee should be on the next rent payment.I have seen so many landlords step over dollars to collect pennies.. you going to evict someone over 50 bucks and now have vacancy with the risk ( depending on your area) that comes with that and the lose of rent.. this to me is just not wise move.. 

Buying out of state could be a very simple, easy & low risk strategy.

You had no idea there was a risk of it falling on her car because you are not a tree expert nor clairvoyant and you never received her letter that she gave to the wrong person.