Is it worth it to go through the proper process with the city and run the risk of a huge expense to make this a 3rd unit? 

It would actually be a net PROFIT given the huge increase to tax revenues. 

This is a huge problem for the buyer.

.• Use some equity from the sale to make this transition smoother.I’m torn between maintaining our current home as an asset and buying  a new smaller house to use as a rental after we move back in versus simplifying and focusing on a single upgraded property Considering factors like market trends, potential equity growth, and quality of life, which path do you think would be most beneficial?

It's a shared house so they have no renter's rights giving the owner huge leverage and control. 

Right now there's huge concentration, but as this continues to build out and we see north of the high 30s GW by 10 years from now it'll be almost a requirement to keep some type of locality based risk assessment and to diversify. 

So huge portion of investment is not even depreciable. 2) All the repairs and property management fees etc are real expenses.

They financed 100% of that transaction, and I took on a huge loan - a huge risk for a broke guy like me.

The Corporate Transparency Act (CTA), which requires businesses to report Beneficial Ownership Information (BOI) to combat financial crimes, is now facing uncertainty due to a recent federal court ruling:What Happened?

Huge Red Flag for me!