I don't want to keep putting money into repairs on something that will never generate a return.

@Ryan Leake i like that idea as well, we do have some priorities we are working at before we start to see what a new app might look like but we once we get to that point we'll definitely keep the community up to date on announcements.Thanks for the feedback

The easiest solution is typically keeping water away from the wall. 

We’ll continue to monitor the data as it comes in and keep our clients informed as the market evolves.Stay tuned for more updates as we continue to analyze the latest trends. 

Want to keep these forever, sell in few years, buy more?

Of the tenants keep it IMMACULATE (do an inspection.)

You likely don't have the net worth, proper LLC management or proper separation of personal interests to make this an effective approach. there numerous BP threads you can search to get more insights. tldr - keep under personal name and get a good umbrella plan. 

Or should I try to keep them completely separate to not dilute the brand of either?  

However, I remember the process of onboarding my properties being a nightmare back in 2020 and would rather just keep my current mediocre manager than deal with a whole new nightmare and still risk them being not good. 

When buildings like this do come up, it's usually placed on the MLS, but you're gonna need to keep an eye on the market for long stretches of time.