@Erich HatchFirst, I look at permit history.

I know certain areas where I live are limiting those types of permits, etc.

A key step is also meeting with the City and/or all entities who are involved in permitting. 

That's a spreadsheet that doesn't transfer to a real life leasing scenario because its not permitted within the zoning code.If the property is zoned RM1, then  perhaps you can lease to 8 unrelated individuals by converting the building into multiple units.

Perhaps they would make more money if STR was an option, however if that's not permitted in their location, no STR demand exists, or no STR PM is willing to take on their property, they may not have that option.

Costs like engineering and permitting can become disproportionately high for mid-size projects.Height and Density: Focus on areas where zoning allows for verticality and density.

Can you take it to the city to get it permitted?

About 6ac of grass with scattered trees, a pretty wetland area, and decently close to larger towns and recreation areas (Ocala National Forest, Mt.

As far as permits and renovations and ADU additions?

I agree, I would be very careful doing anything that is not permitted or allowed based on the zoning.