You make some good points and we will definitely keep those in mind as we get closer to our decision.

If a decision is being made to deny an applicant because of these categories then that could be a violation.

My feedback would be get a few rentals under your belt then make your decision, assuming we're talking about rentals, leverage, insurance and umbrella policy should check most of the boxes you're looking for.  

Of which time is the most important part of the trade off, this is Passive.For most people it's not the ability to do it on their own, its the time commitment to makes the decision. 

The surveys have to be presented first at the required Neighbohood meeting on the Rezoning, then to the Planning & Zoning Departments, and finally to the County Commissioners, who have the final decision on whether to allow the rezoning from duplex to fourplex on the pre-existing fourplex's. 

We were planning on long term rental but made the decision to do STR instead.

That being said, I think the condo route would a better decision.

You'll need this only for a go/no go decision on your 1031.The requirements to defer all tax (a complete exchange) are that you purchase at least as much as your net sale and you use all of the net proceeds to do that.In a partial exchange you are either purchasing less than your net sale or you are taking some cash out of the proceeds. 

BTW--I will provide you with a list of guidelines to help you in your investing decisions.

It doesn't hurt speaking with a realtor to see what the property can sell for and make a decision there.