It depends what your goal is.

We also buy at a discount (pricing depending on those qualities). 

This really all depends on the property type.

Its going to really depend on your location, scope of work, and finishes.

It is really going to depend on your cash position and long term goals.

And the guests are able to stay in a better property than a typical hotel room can provide. 

Or paying off my debt, while I provide them with a nice house to live in instead of an apartment. 

As per their terms of use, "The Site is provided solely for your personal noncommercial use."

All that to say, I'm not sure when they will want to cash in and sell the lot due to the appreciation the subdivision has provided.

This is a physical asset, not paper, and it's providing consistent income.Albeit for your not understanding tax laws and depreciation, I'm wondering why there's a question as to what you should keep.You understand capital gains, but I'm pretty sure you're not familiar with depreciation and loan paydown.