You are so right about analysis paralysis 😁Not too concerned about mechanics though I would like to learn more about how to best use CRMs (specifically freedomsoft), but also would like to learn specifics regarding forming LLC structures and tax strategies 🤔

Instead of jumping into an expensive Long Island market with negative cash flow, consider investing in a Texas market like San Antonio, Houston, or DFW suburbs—these areas offer strong rental demand, lower property taxes than NY, and better cash flow potential.

.- Rents staying flat while property taxes and insurance increase.- Unexpected expenses that eat into profits.For example, some investors who bought in 2022 at high interest rates expected strong rent growth to cover costs.

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

I agree with the others here that say you need to have some skin in the game, if you are going to live there yourself, get an FHA loan rather than owner financing, you can get a 3.5% down loan, personally I do not love these as they require  PMI which is an additional expense, and you also need  bring additional funds for closing at least for taxes, title, attorney and transfer fees . borrowing from anyone else for the down payment, to include a personal loan from the bank is not a good idea, those again will be higher int. rate.

I pay $875 (including principal, interest, taxes, and insurance) and rent it out for $1,625.

It's a more affordable market and lower property taxes, so you may actually have a chance to cash flow.

If the permanent financing will allow you to recover most of your initial investment and the fair market rent covers the principal, interest taxes, and insurance with cash left over, you have a BRRRR.

Check with your municipality about how property taxes will change when you buy the place.

When you live in that duplex for 2 years and then sell you'll be able to take 50% of the profit tax free (the allocation for the side you lived in).