I didn’t panic and sell when I was 60K underwater even though I had a lot of pressure to do so.

Site plan review (even tho the footprint of the home isn't being change) town zoning board and planning board meetings like crazy, the town being afraid that instead of long term housing we will air b&b it, and so on.Negatives:- Will probably be about 30k in the hole when we refi-put an excessive amount of sweat equity into the project-the stress had me pulling my hair out for months-spent a lot more money than expected-taking longer than expectedPositives:-My fiance can now recite all town codes, laws, and zoning regulations off the top of her head-I grew my skills as a contractor/ investor-We made a lot of great connections with people that work with and for the town-created and actually changed some rules and codes in our town to changing existing housing stock and density of the homes to create more affordable housing- Established ourselves in the community as people that are trying to help the community and provide nice homes for people to live- And the biggest of them all I think is we connected with other local inverters!

@Mike Brecko I don’t necessarily agree 100% with the “wear and tear” on air BnB properties.

For 2k a unit (32k total) I can upgrade my electrical in the units to adequately provide service to Air conditioners and electrical conversion to hot water heaters.

New paint, new carpet, new laminate, pressure washing, landscaping, window repairs, fixture updates, sprayed for pests and did electrical repairs.

The stair supports were originally pressure treated pine so we painted them white. 

You can also add air conditioning now or later relatively easily. if you want to add hot water baseboard the boiler pipes and time to install will cost you. if you want to do electric baseboard you might have to do service upgrade to support the additional circuits and amps they draw. 

The hydraulic jacking pump synchronizes the pressure to the jacks so that the whole building will lift evenly without racking.

I am also an Air Force vet, and I am currently working on a master of science in Mechanical engineering. 

@Amanda Webb I can't speak to the regulations but if the primary motivation is ROI it probably isn't worth it you can get better returns elsewhere, if you want to use the cabin part of the time then I would continue the search and understand that it will be an Air BnB subsidized vacation home and not an investment.