If these 2 estimates are REALLY far apart, you can also identify items you have a low certainty about and do more research to raise that certainty and narrow those estimates.

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

Create a simple spreadsheet or written list to compare the features of each and identify the ones that align with your requirements.

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

Hi I'm Benjamin,I have a few issues I need to resolve. 

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

$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.

Sounds more like identify theft.

I've learned the easiest way to do this is ask the owner to remove everything unnecessary for guest use AND give us permission and the freedom to remove items as we see best.Less stuff in the home, less issues and less work each turnover.

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