You used to easily be able to do this with 2 unit properties, but with prices and rates today it's hard to make this work anymore, unfortunately.

Since then, my cabins have tripled in value - worth easily $800K or more, and have produced $696,XXX in rents.  

I have had a lot of success purchasing 5 bedrooms houses next to larger universities and have been able to easily find tenants.

You can EASILY pass several million to your heirs tax free and avoid at least a $1M in taxes if you spend anywhere near 20 years investing in real estate. 

While I do take into consideration all the relevant expenses when I vet a property I still like to see at least $200/door cash flow so I can more easily build up my reserves and have some money to work with.  

JohnFirst look at your states licensing laws, they can easily be found online.

However, there's nothing to be ashamed of; this is a problem that most people encounter and easily overlook, and it can even lead to stumbling, as I got lost there for a while too.

This could have easily been replaced with code/AI.

It currently has a renewed leased tenant for a year @$1400 a month (the owner of the property rented it out to workers at an under-market rate but could easily get $1500-1700).

Regarding the HOA and CC&R's, the builder can make changes to the CC&R's pretty easily while the development is under Declarant Control.