Again I appreciate the advice, but I just wanted to clear up the motivation of the post.  

It's not as if you are going to sue yourself if there's some sort of problem. 

Should I flip the first home, do a BRRR strategy of some sort on it to get more $$$ for another property. 

Thanks to many of you that motivated me to start this journey. 

My goal is to have vacation rentals in all sorts of markets and it is such a motivating goal to have.

We of course could build an internal manual process with a virtual assistant of some sort, but I want to see if anything exists. 

If you told him you have been playing pickup games for the past year and need help improving your jump shot, now he has evidence you're motivated and a specific goal he can quickly help you work towards.

He is all about finding motivated sellers, negotiating with them, and finding buyers.

Unless you have buyer-in-hand or some other mission (e.g. subsidized housing or religious-based motives), I seriously think the risks are way more substantial than most people could handle.

That said, we're not overly familiar with this market, where to look, or what sort of funds would be required to allow a rental to work.Again, some sort of house hack and MTR strategy would be great but open to suggestions.