I took notes what you said, and this really does help provide measurable action steps for me in the near future.

If it is worth 250K now it most likely will be worth more in the future.

My question is, can I do a study on a home that is currently my primary residence and not yet a rental but will become a rental and I use the paper loss in the future when I need it but have captured the 100% bonus depreciation by doing the cost segregation study in 2022?

You have a very good balanced approach to getting started and it's great you are prepping for the future.

Just refi back to 20 or 25 years so your P/I works versus the future property cashflow.I would not sit and wait for a higher paying customer. 

I am putting in place what I determine to be responsible tenants that want to be home owners in the future.   

I don't see any scenario in the future where I don't have to accept some type of online payment, especially because I manage most of my properties remotely and I cater to midterm guests who are usually not in the area when they're sending in their deposit and first month's rent so I HAVE to be able to accept online payments.

.: @Travis Boyd you’ll lose more in interest rate increases, potential property taxes increases, realtor commission and other transaction costs than you’ll pay on any future cap gain taxes.

As for the future of 2nd mortgages, it's tough to say for certain.

I may consider selling off my Indianapolis area SFHs to 1031 exchange to Nevada (Reno or Vegas, looking at those 2 markets) - I think my kids would rather have another home in Nevada (future primary, vacation home or rental) vs dealing with rentals 2000 miles away.