Lease automatically renew week to week and need 15 day notice to terminate. haven’t running into issues.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

I see what the issues are and what needs to be fixed.

I've contacted 8 insurance companies/brokers and no one offers policies (issue being the subleasing).

Non-issue.

Also, our cleaners will report property issues to us through Breezeway and we manage all of the repairs and consumables.  

Therefore, school districts are not an issue. 

$150k is more than enough to get you started, but the issue is that right now it sounds as if it's "trapped" in another property as equity.

Typically  issues are raised when the exterior is not kept up with / parking on grass / garbage in neighborhoods where everyone takes pretty good care of their homes.If you keep it clean and run a tight ship, you should be okay most of the time.

In our experience as a property management company, we allow owners to use home warranties, but they are required to coordinate directly with the warranty company themselves.The main issue we’ve seen is that home warranties can significantly delay even simple repairs.