Im the dreamer (although well researched dreamer) and my husband is the risk-adverse.

As Jay mentioned they must be NMLS licensed if owner occupant of in several states even commercial needs licensing.The NMLS is like the database, each state has a division of banking that oversees lending requirements then you also on the federal level have CFPB as well as consumer protection laws.I want to add that I believe yesterday the CFPB is undergoing changes, but if it goes away that does not mean that many of the laws in place especially consumer protection laws would go away. 

hopefully your inspection went well. wish i would have seen your post earlier i would have been happy to help you out with your inspection. but to answer your question, there really isn't anything you need to "ask" your inspector to look for. if he is a good inspector he will know what to look for and what defects are major and should be addressed immediately and which defects are minor.

Is the higher price agent inflating to get the listing or is the lower price agent just not keyed in well enough in the specific neighborhood? 

At some point if you're doing well, maybe turn the first one into STR or LTR, and do it again.   

He's lived in Japan a few years as well (Fukuoka, I believe).

Would love to connect to hear more about your experiences as well and any PM recommendations.  

You really got to do due diligence right now if you look into Lake Okeechobee Florida and that surrounding area I feel it can go well.  

well as they say  Rank has its privileges.. 

In my experience, most mom-and-pop investors lose a lot of money due to poor management of tenants, as well as poor/deferred maintenance.