My main concern is regarding cost-basis and future capital gains tax when I ultimately sale the property. 

(With several million or more potential clients, if you gained 20%+ of the marketshare.)

This way, maintenance, repairs, and taxes are the responsibility of the new owner, while you continue to collect principal and interest, potentially as tax-free income.I'm not a CPA, just a heads-up 😄, but you could possibly avoid capital gains tax with this approach.

For saving a couple of hundred dollars a year we gain the "privilege" pay $1K-3K in general  deductible and $4K-6K in hail/wind deductible (and likely 80% of the cost of a new roof here in TX).

The lease says that she must gain owners permission if the guest is to stay for longer than 30 days. 

To make matters worse, the IRS will recapture all of the cost-seg stuff that lowered your basis, which means you will be taxed on a significant gain, even though you lost money.

I am slowly building my people around me and gaining knowledge daily.

I understand that how you structure your business could benefit from tax strategy, but how many ways can you buy or sell a property to avoid capitol gains, etc, unless you're doing a 1031 exchange?

It makes sense to harvest that gain, then repeat the process on the next investment. 

This allows you to defer all of your capital gains through a 1031 exchange.Additionally, it’s important to keep in mind that the exchange must be like-kind.