The accounting entry would be debit to interest expense, debit to loan payable, debit to taxes, credit to cash.P&L would reflect rent as income, Less all the expenses, including property tax.

Otherwise it is probably going to be a money loser, or making so little money that it's not worth the time unless you are rent shifting, which is evil but is how the large PM companies manage to make these properties work.Most of those higher producing properties are in the resorts.

Rented it for a few years then slowly started making updates to increase rent.

What about charging another $25 a month in rent?

$3K nonrefundable option money, $825 first month’s rent.

Only turnkey properties which I rent for 1% to 1.5% of the purchase price.

Even better if I can sit down with a builder and get started on funding and blueprints.This meta-strategy will use all the above strategies:1. house hacking: house will be built from scratch to maximize rent/room, while having a family unit/ADU for my family to live in one year2. costseg/STR: the building will be built from scratch to maximize bonus depreciation.

I would also want to make sure that either short term or long term rents can support the full morgage payment, since there is not a DSCR specific program geared to mid-term rentals yet. 

Let me know if you have any questions on areas of Stamford, rents, the market, etc. 

I am not the expert as I do not own a cabin but as a guest (I go once a year usually) I will not rent without a hot tub (or a view).