Found the deal for sale in 2022 and stayed close to it for ~18 months.

Assuming RentingFamilyMember continues to file Schedule E, would/how does that affect the real estate capital gains exemption on a future sale?

Purchase price: $140,000 Sale price: $260,000 We funded this deal entirely through private and hard money, allowing us to invest without using any of our own money.

For the investors making money typically they figure out the strategy and location that works BEST for their particular situation and then go all in on that! 

Without getting into the specific numbers on sale, or year I'd like to share the property appreciation.

If the market doesn’t support a sale in that window, what then?

Gotta do a bit more research to figure out exactly when to cancel them and the amounts that it may make sense to have.

(Search for the Due on Sale clause in a mortgage and you'll see plenty of threads and opinions on that but it is very common practice).I would focus 99% of your time on finding the right area and property, as well as team - agent, Property Manager (@Stephen Glover is a very good start on this one btw), banker, Contractor, etc.

Your loan probably technically doesn't allow this because there is a "due on sale clause" but I have never heard of a loan being called as long as it's being paid My advice to you would be to screen potential property managers, read reviews then set it up to be managed by them. 

I had to abandon their origination software after spending 6 months and 5-figures on it.