It does sound like our scenarios are different.

I have had two different property management companies in San Antonio and they both required to be named as an additional insured or the fees were going to be higher.

They both have their pros and cons and will appeal to different types of people and financial situations.

There are different ways to do hard money.

It's a really big difference too. 

 Once a person lets earnest money  go hard, they become emotionally attached.If you find yourself in a situation, where there was something majorly different than what you realized, then it is my firm opinion that it is best to let the seller have your earnest money and take stage left.Remember, no deal is better than a bad deal.No, I have not always been the master of that particular principal.

That’s $30,000 over the five-year hold.Just for kicks, notice the same value invested in a “high” interest savings account (earning 1%) over five years would earn a measly $5,000.That’s a difference of $25,000 over the span of 5 years!

I also didn't realize how many different skills were required, from financing to managing contractors to permits to city inspections to managing tenants or property managers.

Maybe you can run calculations on condos versus homes in your desired areas or within commuting proximity to see the differences short and long-term. 

Understand that different cities and counties are different.