At a minimum, assuming your buyers are homeowners, you'll want an RMLO to underwrite and paper these for compliance, and you'll want to have an attorney draft your loan documents.

And I’m old school with pen and paper with receipts jammed in folders for each property.

Even short term rentals don't actually cash flow in most markets...you can make it look good on paper, but end of year actual numbers do not cash flow until probably year 3.

I’d run my pen and paper analysis and think: “So I’m going to pay $20k down on a $100k house just to make $200 a month?

It sounds great on paper, but also kind of too good to be true.

IF you are going to hold to perpetuity as the lender, not as important but if you are gonna sell it, clean paper is the best paper.

Unlike all other deductions, you don't directly make a payment for depreciation, so it appears to be some freebie paper deduction.

Start by learning the flip math on paper, not YouTube: find three recent sales, back into ARV, subtract buy, rehab, holds, and sell costs to see your true margin.

From a tax side, that $1,000 loss isn’t really a loss once you factor in depreciation, that non-cash expense often turns negative cash flow into a paper loss, which can help offset other income depending on your situation.You’ll also build equity through principal paydown and appreciation, and those property taxes are fully deductible.

Any cash flow on paper will be eaten up.