I'm leery of high leverage until I get my feet under me and some experience, so I'm aiming at smaller deals to learn the process before trying to hit a home run.

I have not had an issue with the claw back scenario and if I did I would IMMEDIATELY begin the eviction process which I would then pursue relentlessly.But alas, some tenants use this trick after they have vacated your property. 

After discussing their goals, we realized they would like to maximize the property's value while also including me in the process, given my background in general contracting.

It’s a huge renting point and can help you get bigger rents.

When did real estate become simpler for you in your process?

In your scenario, claiming that $117k depreciation deduction could lower your taxable income from $700k to $583k, which is a huge benefit in the short term.As for the RE pro status, if one of you becomes a full-time real estate professional, you can potentially offset active income (like W2) with passive losses from real estate. 

Wholesalers drag out the process if you go with a bad one. they are not buying the house. they only want your signature.

PM's will have plenty of contractors to help streamline the process for you and limit your liability when dealing with contractors. 

I was reading last night and thought:Why should I spend 2-3 years growing my single family home portfolio when I can just buy multifamilies without having to pay the huge down payment myself, instead using the private lender money?

When i read about how their deal was really messed up with most investor probably going to take huge loss's its not shocking.. you have to stay right on top of these and have the manpower to do it.