Other Info: Primary residence in NH has equity of $400k + Rental in NH has equity of $260k+ (Capital gain on $120k?)

The gains would be tax free to your parents, as they owner occupied it for at least 2 years out of 5 years. 

Payments that you make normally fall into one of 3 buckets100% of the payment can be factored in somewhere on the returnPartial payment can be factored somewhere on the return0% of the payment can be factored in somewhere on the returnHouse-hacking also has considerable tax implications in the event that you want to sell this property.You can potentially defer a portion or all of the gain on the investment property with 1031 exclusion.You can potentially exclude a portion or all of the gain on the personal residence with section 121 exclusion

We lost his money on one, and while it didn't hurt the family dynamic, my wife and I hear about it from time to time (the latest being that he is still burning through his losses on his taxes, since he doesn't have enough passive income/gains to use the whole loss yet).Stories I have heard: there are families that have been completely decimated by going into business together, and there are families that have run successful multi-generational businesses. 

Or pay the capital gains and wait a little while and hope for a market correction?

I have had a growing desire to learn more about the real estate business and knew that in the future i would want to gain more knowledge and expand to either more rentals or wholesaling.

I am just starting out but will put in the effort and time if it means I gain some knowledge towards building my own wealth.

Hi I currently have a portfolio deal in my pipeline where the owner is interested in selling his 14 units portfolio at $1M and was thinking to 1031 exchange his 1M into a bigger property so he could avoid capital gain taxes. 

I even sanded the floors myself and it's the last time ill ever do that lol.It was quite stressful living through the flip, but when I finally got it sold with no capital gains (lived in it for 2 out of the last 5 years). 

The realized gain on the sale will be $430,000 - $165,000 = $265,000.