I’m seeing that property crime is pretty high and since I’m an out of state investor, I would have a hard time keeping an eye on the ground besides cleaners/handymen between stays. 

Honestly, these issues you've aired, a cold-blooded "Landlord" wouldn't loose a wink of sleep over.

I'm now working on my second "dive into full-time REI" hahaThe first time I thought that I would be able to generate cashflow out of thin air and that I could half-*** my side gig of being an RE agent for investors. 

We are thinking of doing Air BnB to rent it out and I have looked at what's out there on Air BnB, HomeAway, FlipKey and other sites to see if similar homes are rented out yet for summer 2018 and it appears they are all still not rented out yet.

@Grace Santos what you can do, although tedious, is gather AirDNA comparables and then use google maps street view to see what the actual address is and send the address, the Air BnB listing, and the AirDNA printout for those specific comparables to the appraiser. 

I QUICKLY found that my guests who are working class New Englanders barely wanted to use Air or VRBO let alone talk to a bot or get automated messages.

In reality what happens is you end up paying more for a "clean house" but because you are doing a flip people want new mechanicals (central air, 200 amp electric, pvc plumbing stack) so you end up doing a full gut or larger rehab then simple cosmetics and now your returns have shrunk.In your situation for your first investment I would be ok with a smaller return because of the experience gained, but for the next look for larger profit.

Tough sledding at first, until I took a leap of faith and invested $25,000 into the property to make it more appealing to guests on air bnb and vrbo.

Each place takes quite a bit of work to get going ....finding the right contacts....handyman, cleaners, etc.

Dear [Tenant's Name],RE: External Window Air Conditioning Installation and Removal GuidelinesAs we approach the warmer months, we understand the need for comfort within your living space.