If the covenant specifically prohibits renting out rooms or STRs, you may be restricted from doing so.You should carefully review the covenants tied to your property to understand the specific restrictions.

One thing I did note is my insurance is $3K a year lower due to the monitored fire suppression system in these larger properties versus my smaller properties that sleep 12 or less built close to the same time.As someone who has lived in Illinois twice, the politicians there don't care if people burn as long as they can tax and spend. 

He acted like a used-care salesman - trying to be my best friend at the meeting.

The cash flow is poor for this value of an asset and my equity position.  

They said they couldn't identify an IRA as the owner of an account and were uncomfortable with this unconventional request. 

Careful.

I provide all built in appliances but not the fridge unless it came with one and I don't care about it.

Screen tenants carefully, budget for vacancies, and keep learning with books like The House Hacking Strategy and Landlording on Autopilot.Good luck!

Yes, it's possible, but you'd probably need to get approved in the next 30 days as I'd estimate a 60 day close (at least) for an investment property in the name of an LLC.

An annuity is definitely a different level of risk exposure than this type of an alternative investment.