I'm talking (2) $60K duplexes, and one $125K fourplex all above 2.2% rent to price in fair/good condition. 

Otherwise, you are just gambling that the bank will not call the loan if/when they discover you have left the property (which probably states it will be owner occupied in your loan, if it's a primary) and are no longer making payments. 

How did you decide on a fair purchase price looking forward a year of two?

Around here I normally calculate about a 30% overhead when evaluating a property, but I’m pretty sure I’m gonna have to bump to 40% to cover the increased insurance cost there.I’ve seen a fair number of SFRs that look like they would provide 8% gross using the only tools I have available over here, which is rentometer and Zillow.

I don’t want to mess around with homeowner grade stuff from Lowe’s or whatnot, and am willing to pay a fair amount to start getting these under control  professionally. 

Look for similar properties nearby on Vrbo and Airbnb to see how they are doing to see how this might fair as a STR.

The issue I face is the guest house is fairly small but fine for a single individual.

Are there any resources that exist to determine what the fair market price for a condo should be in a particular area?   

4) What will be your screening requirements to comply with Fair Housing & local statutes?

That's what I think a fair price is.It does depend on how far it is to the roofing supply store, how far it is for the workers to travel, if there's any rotting wood that needs to be replaced and how busy they are (busier = higher profit).You could buy a couple ladders, a compressor, a 100ft extension cord (14/3), 50 ft of rubber air hose, a roofing nail gun, a caulk tube a couple shingle removers and pick up some day laborers who know how to roof.