Our long term goal is to purchase and move to a remote ranch and for me to be able to quit my job around 40 years old.

My end goal with wholesaling is to eventually buy properties myself.

We moved from CA to AZ last year and have got 2 STRs in AZ going very well.

Move tenants in immediately and same tenants are still there.

If losses strain your finances, selling might be the best move, but optimizing rental income or tax deductions could make holding worthwhile.This post does not create a CPA-Client relationship.

I get get really good prices for home games, graduation, ceremonies, moving kids in and out etc.I get all these bookings from VRBO.

Once you're ready, create a goal (e.g., "I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it.

Outline a clear exit strategy to meet your long-term goal of retaining the property for cash flow.Work with a CPA to ensure tax efficiency, particularly around depreciation, capital gains, and partnership income.

Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

We completely gutted and finished the basement including adding a kitchenette and 3/4 bath, moved out and are now renting both apartments.