I self manage my few properties and have not had any issues at all with the City of Indianapolis. 

I know conventional lending could become an issue depending on the condition of the property.

What issues would there be if I put MY NC house in the LLC that has his name and my name on it?

It wasn’t an issue of “underwriting does review a file until it was complete”.

I doubt if you'll have any issue with your hold period since it is all about your intent anyway.

Since you’re considering converting the upper unit into a short-term rental, you may also want to implement strict rules around smoking or strong odors in your house rules to avoid future issues.

In general it is not worth building a single ADU for a variety of issues but the largest is the cost to add the ADU is typically far greater than the value added by the ADU.  

I keep reading about all the weird financing issues in this space so I wouldn't actually put money in until mid 2025 or later.  

This keeps them motivated.Clear Contracts: Make sure your contracts have deadlines and penalties for delays.Regular Check-Ins: Visit the site often to catch issues early and keep things on track.Scaling UpMultiple Contractors: Work with more than one contractor to avoid delays.

The brother was fed up and needed to sell, but there was a significant issue.