Background: looking at area where log cabins quite popular, so getting comparables should not be an issue. 

I don't know what the ten year appreciation rate will be, but I'm betting it will be insulated against any negative macro trends and positioned to outperform other markets, over the long term. 

Painted (some shade of white) trim will be more popular with tenants than stained wood.

I'm not a lawyer but I bet he could sue you if you don't let him move in and have a case.

I'd bet you'd be better off getting separate loans from the same lender when it's all said and done.

If you are at the stage of your life that it makes sense house hacking is your best bet. 

Trying to go no HOA would be your best bet if you really wanted to puruse this strategy. 

A lot more popular and many color options.

While I’ve had a few frustrating issues with B of A, the convenience of their online platform, and their available services, have led me to stay.That being said, I’m willing to bet that the contractor has deposited quite a few checks that were returned for insufficient funds; stop payment; etc.  

I’d bet your also not quick to take care of any of the tenants needs without bitching about it.