@Tom Rairdon If you’ve owned your short-term rental (STR) for over a year, it likely qualifies for long-term capital gains (LTCG) treatment, taxed at lower rates (0%-20%) compared to your 33% ordinary income bracket.

Question: Should I collateralize the loan (if using private or hard money), or rely on roll-over loans (to maximize the lower points and 3-4% rate)?

If rates come down (most likely not in 2025) you can refinance or just shovel cash-flow and pay it down quicker. 

Interest rate- prime plus? 

Check their occupancy, nightly rate and amenities.

The cost of labor , materials , property taxes , inflation , interest rates  etc .

Many of these lenders allowing 2nds behind them are more expensive capital (10's - 13's in our current market [high rates - but now showing signs of coming down]).

There’s a lot of construction, which could hurt both prices and vacancy rates.

What interest rate are you getting?

Misinformation stating that the guru dropped out of school, was fired from his job, failed in his business startup, but when he discovered” the “secret” of real estate investing, met with almost instantaneous success7.