We will most likely be doing a long term rental.

I think you'd be better served to turn the STR unit into a long term rental.

Most people just use the term but there is association management, apartment/ Multi-family management and then property management.For instance, in Florida, you need a license to practice Association Management (in most cases) and a real estate license to practice property management (in most cases). 

Is it okay to make that investment and wait for a long term appreciation?

And or course, short term loan for HELOC and then refinance later.

We're also able to evaluate our rates, and keep pace with inflation, on a monthly and quarterly basis because of shorter term leases.Now we syndicate larger self-storage deals and work with passive investors.

I know it is crazy to think but is there private lenders to talk to that will work with you on rates, terms...etc?

Loan terms are going to vary, based on the asset, your liquidity, net worth.We've got three deals currently under contract with a credit union, 25 yr am, 6.75% rate, 2 years I/O, 5 yr term. 

The downside of this strategy is that the borrower has some leverage to negotiate terms that benefit them in exchange for the Deed in Lieu.Plan executedGiven that we had ruled out the first two options, it became clear that we were going to end up taking these properties back along with inheriting any accrued liability.

I have found that most section 8 tenants, want to leave on good terms, since their address history follows them around.