- Loss of historical data (for both IRS audits and for personal portfolio tracking.)You should be able to print the general ledger and Balance sheet / income statement for each period.

The loan has a payback period of 5 years in equal installments. 

My grandmother wants to sell her home but live there rent free for the rest of her life.

Aloha @Daniel Kam - most of Kakaako has a 180 day rental minimum, so if you haven't checked with your building association, I recommend you verify what the minimum rental period is for your building.If you are allowed to rent for less than 180 days, you will then need to apply for a GET license, and well as TAT/OTAT and pay the appropriate taxes on a regular basis.  

What happens during periods when the demand for legal work is lower?

The fact that it's not always on the same list as the rest is crazy.

That means their pricing tool is designed to price beneath the rest of the market, which drags the entire market down, especially when combined with their algorithm changes a couple years ago that made pricing (IE lower prices) the #1 factor in ranking.Even if you use an external pricing tool, it gets dragged down by the people using Airbnb's pricing. 

By lending money on quick turnover deals and running JV's I should be able to fill some of the latency period with needle moving activity.

We all knew the rest.

As you may be aware, the City of Asheville (about 2/3 of Asheville is in city limits; the rest is under county jurisdiction) has had strict STR regulations in place since 2016.