We also take on the responsibility of doing maintenance, and caring for public areas.

They also care about their clients and keep things affordable for investors. 

Sure, I get that if the deal is good, who cares... and no one likes inherited tenants anyways, but I wouldn't mind a little more protection during the purchase.

This is definitely more of an estate planning issue than REI.You'll want to discuss with an attorney of your choice.

We have been property owners for 3 years. I did a 1031 exchange to purchase 2 properties totaling $260k. We have a total of 5 properties and are looking to add more. We have been looking for the right properties to pu...

My question is, with all the moving parts: financing, permits, zoning, platting, building - how would you start thinking about and making sure all of the costs are taken care of and you’re not missing anything?

As far as formulas, at the end of the day, all you should care about is Cap rate or NOI.

Does anyone know of an investor friendly contractor that can be recommended? 

After you get a house under contract take it to your title company and they will take care of the rest.

Johannes,If you have to make changes to the Association, I know of an couple of Attorneys in CT that have handled formation of these small (2-3) unit condos.