Over time as you walk hundreds of these old homes you will be able to spot right away the issues and appreciate the great work already put into the property. 

The skills you learn on repairs are what let you do a walk-through inspection on a future property and spot problems before you even make an offer, let alone spend time and $$$ on an inspection. 

This is not the same rental market as Boston, where a 2 bedroom was your sweet spot.

My question is, if we went back out to family and "vacationed" for a month or two before our 2 years was up, could we still qualify for this exemption?

My risk tolerance is usually pretty decent, but given the stakes (of being unable to find alternative financing), I can’t seem to mentally let go of conventional lending options.The risks I anticipate are: 1) Credit score will drop with a lot of activity in a short time (though I don’t know how much), 2) The properties are pretty rural, so appraisals could be low or lenders may offer lower LTVs because of the rural classification, and 3) Sudden market shifts could make lenders skittish about vacation rentals, making it more difficult to secure non-conventional lending.My questions are: 1) How confident can I be that I will be able to secure a DSCR loan?  

The city assigned a detective, and I thought this would be an easy thing to resolve since we know they get off the bus (some days) at the same time/spot.

I'm from Los Angeles, but I've taken several trips down to San Diego over the past year for vacation. 

Dose anyone have experience potentially charging to rent these spaces out since they are covered spots within the property and not just a lot on the back?

or do I buy the second property as a vacation property??

But I doubt they’ll ever get banned in a vacation area.