Our mortgage payments started at $2300, but due to increasing property taxes and insurance, they have alarmingly risen to just under $3300.

After two years I understand for tax purposes I sell it as a rental.

Now you have a brand new property that has no mortgage, rents for $2,000 a month with $300 a month in taxes, insurance ect…profit $1,700 a month.

You look around every corner and someone has a mortgage note / debt fund.

I'm curious if the income from these rentals, listed on Schedule E, will be factored into my Debt-to-Income (DTI) ratio.

There is no problem with a NonQM wholelender or a broker to do a 5+ to 30 unit STR.It would be a DSCR loan and I love the Airdna report that can help get your loan to debt service.There are options of looking at rent rolls and or statements from Airbnb, Vrbo and so on.

Is there a certain neighborhood, owner occupied vs. not owner occupied, length of ownership, debt on property vs. no debt, etc.

Im in NJ, but not sure it's the right market for me due to very high taxes and cost of houses. 

In your case you have a lot of losses in the time you own the property but these losses transfer through to your personal tax return, so you can recover some of it and not have to count the full nominal amount.

Heck, you gotta pay taxes on it too, and you also run the risk of the unforeseen and problems along the way with a rehab.Lets see, I paid my fees and got back on MLS last May, and signed up for Privy.