Two, the owner is responsible for the means to keep grass cut during the growing season.

Or is it simply just asking for the payoff amount and cutting them a check for the refinance given the property appraises? 

I feel weird buying a vacation home for ME when I feel like so much of my strategy is 'work hard, save money, build equity, expand REI' - but at the same time, this could potentially be a small income-generator from AirBNB - I just don't have enough faith in that to really push me over the edge into moving forward.

Yes, wood siding is more subject to moisture damage and rot, but you can pretty easily cut out a section yourself and (hopefully) replace it with an exact match.

I wont lie....half of it is a dump outside full of cut lumber and shrubbery.

From what I can see on google maps, the street itself actually doesn’t look too terrible and the city has been cutting the grass at the property (which they have been charging for). 

I’m assuming that because the investor cut half the funding that he will receive 50% of what the original equity/cash flow. 

Cut back hours from the 9-5 and pick up more working for a property management company.

That kind of thinking puts all of our safety at risk.

All those services you mention are going to cut into your profits.