Also, the short answer to your question IMHO is as early you possibly can haha

This works best when the seller is motivated and open to flexible terms.4.BRRRR Strategy (Buy, Rehab, Rent, Refinance, Repeat)– If you find the right undervalued property, you can finance the rehab with short-term funding and then refinance into a long-term loan, pulling most or all of your money back out.5.House Hacking– If you’re open to living in your investment, you can use an FHA loan (as low as 3.5% down)to buy a multi-unit, live in one unit, and rent out the others.

Hard money loans are another option for short-term financing, especially if you're looking at fix-and-flip opportunities.

Bought it as a safe bet thinking it would do roughly $35k annually in short term rents.

Partnering: If you're initially short on funds or experience, consider partnering with someone who has more experience or capital.

Heather Skowronsky In short, it falls down to a personal opinion instead of an official statement.

That is tight leverage for an investment 2nd position loan.A private investor might be willing to do it, it's not going to be cheap at all & will be short-term money & will not be a line of credit to take out at your liking.What is your rate on the 1st?

@Desiree Board For your mix of long-term rentals (LTRs), short-term rentals (STRs), and house flipping, an LLC is ideal for liability protection and pass-through taxation.

We are now doing short term rentals but we're thinking about changing to a small wedding venue. 

NYC laws around rentals—especially short- to mid-term—can be tricky, so you’ll want to avoid any compliance headaches.The biggest challenge with this plan is finding a rent-stabilized apartment that makes financial sense and actually gives you breathing room.