Look at the following indicators over a 10-15 year period to understand trends: population, job growth, job diversity, income growth, median (not medium) home price, crime rates, and vacancy rates. 

Rents are strong there and it is a diverse city for employment. 

However, I think we are are generations away from a real shift culturally especially with bigger companies and conglomerates that are still run by people that think "the internet is a fad" or something. 

The culture and lifestyle is amazing.

The cultural shift you have hypothesized simply is no where close to having occurred yet....and the hypothesis that the coronavirus will hasten it, has done the exact opposite in the last 4 weeks. 

STRs have great value in a city like Boston as we have year-round demand for short term housing due to a diverse economy.

It’s a great city with diverse employers and business friendly laws.

Florida is about as diverse as California is with dramatically different markets.

Folks who move from the Northeast down to Florida, realize that most of Florida doesn't have the weather, the low cost of living or the culture they assumed it had and end up moving half-way back home. 

I suspect the culture in Ohio will be similar.For "systems" I'd say to make a standard packet of info that has a sample lease, floor plan with square footage, list of "features" like what appliances are there or if there are storm doors, etc., an introduction letter, and an application.