What would you conservatively estimate the main home/rental in the back would bring in on a monthly basis?
I know the area pretty well and seems as though $1900 would be conservative for the main house. You did say you put $70,000 into it, so maybe it is a nicer unit and could demand more. And then you have the other property. Long-term rental you are probably looking at maybe $1400 conservatively. Obviously it is a unique build but it is also small, so let's estimate low. So, all in you could conservatively bring in $3400 gross income. Granted, this could be substantially higher with a successful STR & if your primary is more of a luxury rental, but just estimating conservative for the time being.
What is your debt going to look like on a monthly basis for those properties including the refinanced mortgage + loan + etc.?
It is hard to know what would be a good decision without knowing some more details. Good luck!