That said, we understand that insurance details can sometimes be complex or overlooked during the decision-making process.

Should I sell and 1031 the equity into a apartment complex where I can increase my net per month?

Look around your town and find some relatively new apartment or condo complexes- who built them? 

The sheer complexity of this matter alone is enough to illustrate the problem, but this is just the tip of the iceberg.

There is a condominium complex that is fantastic for short term vacation rentals.

Does the condo complex have rent to own percentage restrictions (they all do, you want to know what percentage is allowed and what percentage it is at now)?

For example, if you have no experience in land development - that is extremely complex and risky compared to owning NNN rentals. 

From my research, I'm seeing $100-$150/sqft depending on complexity and material.

They will put it in your bank account. at a higher price, Airbnb is mostly crickets and booking.com continues to bring in good traffic booking.com has been very smooth and the whole review mantra with Airbnb is almost non-existent yes somewhat complex to set up.

Whether that is actually true can be debatable and the seller might not want to deal with complex lending situations.