Block is still a good insulator, water/termite resistant, and hurricane proof, while there's room for improvement in windows, insulation, AC efficiency etc.

The STR one is 1989 built and needs some Rehab in form of paint, cabinets, appliances, floor, fixtures, water heater etc.

People don't want to live in a basement.

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Would a hot tub be easier to maintain / more desirable?

Do that every year until you are tired of house hacking, then find a SFH you want to live in. 

I lived there for almost 10 years before moving to NJ.

If you didn't get an inspection and you plan on living in the property immediately or someone else lives in it immediately, you need your homeowners insurance to accept the condition of the roof. 

I would just put a few more snap traps around, seal the holes to the exterior that the mice are using to get in and out (sprayfoam is your friend for this), and make sure the tenants remove any food or trash, water, whatever is attracting them.

. - Available for FHA - 23 years old, live with my parents and I love it, as do they, so no rush to move out.- Hard/smart worker.