More specific ideas for business that still operate these days: scrubs shop, medical equipment, bikes shop, pet stores, hardware stores, nurseries, beauty supplies, dollar stores, cannabis store (if legal in your state) or CBD products store, vape/smoke shops, doughnut stores, Fitness equipment store, pop-up COVID testing centers.Bonus round:If your location has a big parking lot, you can set up a "movie drive-in" on some nights and have the businesses in the strip serve the food/drinks.

I love geeking out on marketing technology, creating and automating processes, and testing different marketing strategies online.

You may not be able to get the higher rent even if you fix them up, so maybe start out by getting all units in good "rentable" condition, to test the market, and then migrate up on rent  over time, to start out easy. 

Some tenants I've spoken to, use security deposits and the ability to pay a security deposit as a bit of a litmus test for a good renter, but I can see how those types of products can open up the number of tenants you can accept!

One thing you should definitely do is put a test ad out on Facebook marketplace and Craigslist to see what the demand would be for what you are offering. 

Tests had to be done on the studs in different areas of the house. 

When you meet with the contractors, make sure to have them help you understand what you have, what will be required to repair and maintain what you have, and what you should be budgeting for future capital improvements, if needed.Alongside our inspections, we are putting together the strategy for the park, performing our rent survey, running our test marketing to understand the demand in the market, and creating the budget for the project.All the best, Jack

Does this pass the smell test with those who have more experience or am I being to wary?

At that time you could go straight for a broker's license if you passed the test. 

Each space is approximately 300 sq ft and are single rooms with a 3/4 bath.We tested the response and it would be no problem getting tenants/room mates in the spaces at about $1,500 each.