She trusts my financial judgement.

More than likely, you will be out the time, the court costs, any lawyer expense and come away with at best a judgement that will costs you more money to collect.The best route is to talk to the GC and if you cant find common ground, part ways and find one that will in fact finish the work. 

There is a saying in Belgium : “when it rains in Paris it drips in Brussels”. 

It is also a huge benefit for your personal brand (let's be honest, we live in a judgemental society).  

I see you are looking in downtown and many streets do have a tendency to flood during storms or heavy rain.

Keep in mind most good businesses are not for sale that’s why only 20% of business for sale actually sell. 99% of the time a business that’s on the market is not a going to be a good deal so don’t base your judgement around what you find “available”. 

It doesn't look like you would be getting much from the sec121 exclusion.Not sure how selling this property would get your more funds into your Roth IRA, unless it just because it frees up money to make the contribution..If you need funds to build up a reserve / rain day fund / etc., this might be a way to go... 

The cosigner refused to pay, I had to renew the judgement, but he finally wanted to refi his home and had to pay me plus interest for all those years to refi his home.

If you get a judgement you need to collect.

In my state if the tenant does not show we are awarded the eviction and can place judgement.