The smart play would be to build a two story wood frame structure on top of piers or concrete block in most cases. 35 feet is a pretty typical height limit in most neighborhoods, so depending on elevation you SHOULD be able to build two stories on top of the elevated foundation.

Quote from @Gerald Wallace: I'm playing Devil's advocate and running your numbers through the worst-case scenario.

Properties north of Greenridge St. are a fair play. 

I get the whole 'dont fall so far behind market value' narrative but this is a long term play for me to gradually trade less of my time for w2 income if you will.

Go learn how to be nicer or go play in traffic!

Maybe play dumb a little "I don't know if I'm in the right place..."

Here are key factors to consider when searching for a reliable broker.A good private money broker plays a pivotal role in facilitating real estate investments, serving as a bridge between investors seeking capital and private lenders willing to finance those investments.

Two factors at play here.1) STRs generally appraise as residential homes, not as businesses based on multiples. 

Often times, I advise folks to start with HML or PML and the refi into a DSCR loan with a bank/CU when the property is stabilized.I am going to assume that a HML/PML loan would be at a higher cost/rate than a bank that would play ball, so I would prefer that if possible...

I have only done a few deals but the thing I constantly having to remind myself is R/E is a long game.