Homelessness is not an issue.

Ran into a similar issue as you back in 2021 when I was living in San Francisco.

The issue is the down payment is over $250k and no one has that or is willing to fork over that amount.

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.  

There are probably a lot of hidden issues wiht the house.

If you are deadset on refinancing into a conventional loan, then you will likely run into seasoning issues.

It also allows the manager to work directly with the insurance company to resolve issues efficiently.In Texas, this is part of the standard Texas Board of Realtors Property Management Agreement and is considered an industry best practice.

One downside of MF can be the age, and insurance can be a big issue.

There are also ways to go about mindset shifts if that's a serious issue, but I don't know, it sounds like you've spent time with this property, you know all about it, and you have a bunch of other stuff going on in life.For instance, you decide not to raise rent all the way to market rate....This is probably a good move if you hate maintenance calls and your tenants know to handle some maintenance themselves because they are getting a bargain deal.

Tenant issues?