Umbrella Insurance: Yes, having umbrella insurance is a good idea.

While buying near a hospital can sometimes be a good investment, in this case, the hospital in question is MetroHealth, which is a county hospital primarily serving lower-income residents, many of whom are on Medicare or may not have insurance.

I'm also asking for contractor, CPA, insurance, and legal references from the property managers and will speak with / cross-reference them before going forward with one. 

I'm eager to start the work of finding a drive-by appraiser and calling title & insurance companies to close this transaction.

In California, insurance companies are very tough now.

Our lender required us to have title insurance and this week my wife will be submitting a claim! 

I buy supplies, and keep up with pricing, do repairs, except for electrical, plumbing and A/C.

As you stated, that leads to higher property taxes and higher homeowners insurance as well, and when combined with higher property values and a 150% climb in interest rates, it compounds affordability issues.

Also, the costs in Florida are high, with expenses for insurance and the hurricane risk adding up.

Your new potential guests are insurance companies for homeowner displacement (flood, fire), buyers looking to move to the area but not sure where they want to be, sellers who want to sell but have nowhere to go, contract workers in the area, adjunct professors on a semester job, etc.