They do the hard work while investors like myself get the benefit of having a long term rental.

I am today years old in terms of this forum and it's already provided a wealth of super useful information.

I currently own one side-by-side duplex in Euclid (purchased end of 2022), and am looking to eventually buy more rental properties, and possibly get into medium term rentals.

Your loan officer should know these things too...hopefully.  

Hi there,I plan to purchase a short-term rental in Hawaii.

Places like Maplewood, Richmond Heights, Affton, etc. would be where I would start (if looking at long term rentals).

Looking to connect with strong mortgage broker who specializes in loans for investment properties in NJ. 

Long term friendships with local realtors How did you finance this deal?

There are many ways to avoid taxes, so nobody can give you a complete answer without knowing your entire tax situation.If your only taxable item was selling this condo, you would owe long-term capital gains on the $150,000 plus ordinary income on depreciation recapture.

Assuming they could finagle a 10% down payment loan and put up 95k, they'd owe 855k and have close to 200k in equity.