It is facebook that has a rediculously advanced algorithm that can fish your ideal audience from the population better than ANY HUMAN POSSIBLY could.Man if you could only understand the facebook algorithm.Think about it.

I suspect two things are happening here: 1) Hotels are lobbying hard to squeeze VR's in this time of crisis and 2) the Governor made a calculated gamble that STR's are many small fish who, individually, are unlikely to sue while Hotels would certainly do so. 

We also get top dollar for the summer months.Surprisingly we rent out alot in the winter spring and fall.There are major fishing tournaments that bring us extra bookings and people who just come up to fish.We have a covered boat slip with a lift where my boat stays unless someone asks to use it.We make improvements every year to make the place nicer. 

The house's main heating comes from oil and it still has those clanky radiators in every room that act as big eyesore (to me at least)!

The downstairs unit needed a new bath (done) and I plan on also redoing the kitchen as well as splitting the HVAC (One oil unit currently).

I wish I was handy, but me and fixing stuff is like oil in water, it just doesnt mix well.

Rather than fishing for ideas for your particular situation on the public forum (some of the feedback you'll get will be wrong), you should get one on one with knowledgeable tax expert who can analyze your situation and provide you with proper guidance. 

You are two small fishing boats in the Pacific Ocean.  

I do have some large expenses coming up in the next few years such as replacing the oil boiler with a gas boiler (the basement floods a increasingly and the oil boiler is oddly the lowest point intentionally) and the roof is probably 5 years out maybe a little longer.I’m grateful to be in this position and honestly got very fortunate with how the cards rolled out on this one.

Here is info:VT multi family 4 units all 1 bed/bath2 units with oil include heat in rent at $800 for one and $825 for other2 units with propane tenants pay heat at $650 eachTenants pay electric, cable, garbage etc.Income is $2925Expenses are:Tax - 303Ins - 200Utilities - 427Vac - 234Repair-146CapEx -292PM-292Mort-490Total - $2384Cash Flow- $541541*12=$649220%= 26600Closing = 8100Inspect = 500Total 35,200(6492/35200)*100= 18%Looks awesome!