You might find that installing a mini-split system, properly insulating, and ensuring the finishes match the main home’s quality will make a difference in how the appraiser views it.

Diversifying into different markets, like Omaha or Austin, can help reduce any lender concerns and also spread your risk.Have you thought about the specfic market for your STR or MTR?

They are good for comparison of different assets and limited in telling you when, where, or how to invest.

The only real problem I ever had was one time I got some tenants who had significant cultural differences than everyone else.

Every investor  has a different risk tolerance, comes from a different financial situation and has different financial goals.

Be interesting to see the inner workings of the deal and how it was underwritten.The big question in life, not to be or not to be, not nature vs nurture, no, what is the difference between a HML and a PML? 

I've been at 100% occupancy for my small spaces for the past 5 years.My only feedback is that $2 per month per sq ft NNN seems really high to me, but each market is different. 

@Jonathan Carter I looked in a lot of places and I realized that many laws and rules can be interpreted in different ways.

Different lenders can serve different purposes. 

You'll have far less competition as you move into the 5+ unit space where the different financing and higher prices weed out many of the first time investors feeding on $400k fourplexes.