Trash out, touch up paint, replace carpet in 1 bedroom, replace 1 light fixture, replace burned out light bulbs, lawn service, power wash porches driveway & sidewalks, make ready cleaning, staging and on the market in 2.5 weeks What made you interested in investing in this type of deal?

Quote from @Neil Louis: Don't forget the power of networking! 

Dan Powers - New Western

But to the north, west and south, there has (almost) always been a stock of housing that was more affordable than in Boston.But then all of that housing stock kept rising in price, and earning power didn't keep up. 

You will need to run power from the last pole to the power pole beside the trailer.

If that's the case, the easy answer for "next time" is make sure you have a LL account with your utility provider, which will turn the power over into your name if the tenant disconnects from their name. 

I’m feeling overwhelmed with beginning and not sure where to even start.

switch the zoning or rezone to hotel or a permitted grandfathered zoning instead of looking for the license go bigger and get it permanent not just one unit. loophole but very powerful how a lot of condo development is moving forward in miami they are hotels technically 

Savoy investors use them for additional fire power when buying deals.

There's oddly a lot of This is very true, with this large amount of capital, need to think big like NFL player level.I read financial proforma of class B hotel in Maui, it's pretty darn good, in fact it's perhaps the top ten best performing hotel in US in term of vacancy and RevPAR.STR and stuff like that is more for small investor like us with half to 1 mil buying power, but when it is above 5% you really need to talk to some serious developer/realtor in the island and understand the business.If I have that size of capital I would import contractor from California to finish my project in Kukio LOL Currently in kona there're only few new construction that can still being built, I guess it is selling for 1.5mil and above.