Analyze these types of properties in your chosen market and become an "expert".

It looks like a compilation of reports, so the results may not support each other.However, I certainly support your primary assertion that most properties could/should consider the benefit of allowing pets, at least of a certain size/type.

The process isn't complicated - but managing shady Cleveland contractors isn't ideal for people with high-tempo careers LOL That's why I'm trying to get a gist of the different ways people do this. 

I'm seeking recommendations for types of businesses either to encourage/court or to consider myself or with a partner.

HOAs can also enact rules restricting rentals - many of them don't allow any type of short-term rentals (if you were considering AirBnb).  

Not sure if someone out there or a local company specializes in these type of transactions?

This seems like an ideal situation, as I was already considering the idea of a vacation rental property.

In an ideal world you would keep it and then scale up over time (stacking method).

Any factors making the area undesirable for this type of investment?

As for contractors, it would be ideal to physically see previous completed work and current projects.