For the purchase of the new property, you can consider a seller carry offer (balance of purchase price minus the down payment) or obtain a new mortgage on the commercial/resort. 

High level $200k for a $36k gross return is a low yield..however I think there are a few variables..with 35% down you should be able to get stronger lending terms, if the seller is workable you could entertain a concession towards a rate buy down for lower obligations, possibility to look at shorter duration (ARM) loans if you only intend to own 3-5 years which could also offer a lower rate.

On top of that, families have privacy, places to eat together and gather, plus entertainment options right in the home (pools and game rooms). 

Thats a good question, Just purchased Batchleads.io membership to give it ago, So far it has the Skip Trace feature and able to obtain mortgage and lien info of leads but, I though it was fine and dandy until I wanted to see how the current MLS data reflects on there.

We also had an extra umbrella policy.Now that a few years have gone by and we've obtained more assets, meaning we have more to loose, it's made since to start an LLC and start to move things under its protection.Even if you get a good management company, which sounds hard to do, you'll still have to manage them and make sure they're staying on top of things.

As to the HOA you should have been provided or allowed to purchase the HOA documents prior to submitting your offer or obtained them during the study period.

I currently still work as a superintendent but my wife and I both dream of owning our own real estate and obtaining financial freedom that way.

Please let me know if there are any recommended sources to obtain business lending for start up businesses and provide assistance to maintain healthy business credit. 

If he threatens your tenant's life your tenant should obtain a protective order from the court.

He said he hadn't given it much thought but would be willing to entertain a discussion.