It's difficult navigating the home purchase process in general, but a lot of more difficult buying something with costly surprises you didn't plan for. 

Finding a lender willing to do this was quite difficult, but ended up finding FGMC http://fgmc.com .

Cash flow is possible but for an average investor, it is very difficult for returns to benchmark.

It’s difficult to get a line of credit on an investment propertyI would just get a PM and pay them to manage it.

The contractor is required to provide a 1 year warranty on labor and materials but replacement contractors are difficult to find because they have to warranty all the work ... even from the OG contractor. 

You’ll want to talk to a CPA to help you estimate what your tax burden would be in both the under and over 2yr scenarios, see if you qualify for a partial exclusion, etc.It’s difficult to blindly say hold it or sell it now if you don’t have a full picture of what your tax burden.

A good manager reflects on your home and agents will be more likely to place a resident into your home just by knowing the manager running it - even if they have no idea who the owner is.The caveat to all this is that it is very difficult to find a good manager that needs a job.

However, I know this will be very difficult to pull off and is a high risk, especially since I'm already using a lot of time for my full time job and building up my insurance agency on the side after work.

So, its difficult to handle sudden changes in their expenses.

Something that makes my situation a bit more difficult is that I have a job in Hawaii (6 hour time difference from EST. right now).