Once I’ve gained rental income, I would like to finance a Condo and even more rental properties with my income from rentals.

You cannot (legally) exclude your capital gain when you sell your NJ house next year. 

You need to be talking with a broker who has access to a bunch of lenders vs a lender who only has a couple of DSCR outlets. 

What is something that you thought was true about the real estate industry / investing, but turned out to be different  / not true once you actually gained the experience?

Real estate investors are attracted to medium-term rentals to gain the benefits of extra cash flow versus long-term rentals while avoiding regulatory risks, high turnover, and intensive management of short-term rentals.While many investors are now turning to medium-term rentals to build their portfolios, the lending world has unfortunately been a little slow to keep up.

It's one of those necessary steps that can be a hurdle, especially if your funds are tied up or you don’t have immediate access to liquidity.Here are a few strategies I’ve seen work for those in this situation:1.

.- Quality of Life: Milwaukee boasts a vibrant cultural scene, great parks, and access to Lake Michigan, making it an attractive place to live, which can boost property values.- University Presence: With several universities in the area, there’s a steady influx of students, contributing to demand for rental properties.- Tax Incentives: Wisconsin offers various tax incentives for real estate investors, which can improve the overall return on investment.Overall, Milwaukee presents a mix of affordability, growth potential, and a strong rental market, making it an appealing choice for real estate investment.

My understanding is the seller bought with seller financing significantly below market value and has the capital to pay the near due balloon if needed.The seller is the one who proposed SF due to (I assume) capital gains. 

You might lose more than the taxes if you’re in the 15% capital gains bracket. 

The long term capital gains rate for many people is Federal 20%.