I'm now taking out cash and funding the rest of the fix up, as well as going to gain significant cash flow.

I was interested in this topic as well, hopefully we can gain some insight to this.I'm wondering if you're able to achieve anything that would cash-flow as oppose to an appreciation/break even cottage play considering the short length of the rental season. 

I plan to sell quite a bit of stock this year (2024) in order to fund some renovations and want to use the depreciation of these properties (if possible) to offset my capital gains when i sell the stock.

When you donate appreciated securities that you have held for more than one year, you can avoid paying capital gains tax on the appreciation.

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

If you turn it into a rental, think about the capital gains implications. 

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.

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.