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. 

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

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

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

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.

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

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.

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.

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?