Maybe I should recalibrate my strategy for my pennies.

Clinging to a poor investment is as bad a strategy as making the poor investment to begin with.  

Lima One has extremely flexible DSCR loan options, which can be tailored to each investor's needs and investment strategy. 

@Walt Viera, read "The House Hacking Strategy" by Craig Curelop to understand the overall investment concept. 

SO...how do you use City Plans and/or tools when developing your strategy, target market analyses, property acquisitions, etc.?

I spoke to him and he's probably willing to carry anything above the $90K, but he does need that amount in cash.I suppose the main strategy would be to go and get a loan from someone willing to sit in 3rd position. 

What would be the best strategy?

My initial assumptions are yes, based on the “build to rent” strategy.

Your ability to be a resource hub of GCs, title companies, insurance agents, disposition strategies, etc. makes you invaluable.

However, one great strategy I have seen is getting a mid term rental for the slow season, and then going back to STR during the hot season.