I’m a researcher by nature and everybody I know tells me I over think things but most of them hate their W-2 job and are doing nothing to get out of it.

Just google "local community banks" or something of that nature. 

Or look larger into a quadplex or something of that nature?

With the RTO, what I'd love to do is sign a standard year to year lease, and then another lease/lease option/installment sale contract that would give the tenant the property in 30 years in exchange for an initial fee or a monthly fee and them assuming maintenance, or something of that nature.

I think it also depends on the amount and the nature of the deal. 

Its transactional in nature meaning if you quit flipping, your income goes away.

Typically above ground pools do not need to be fenced off as they already have a natural deterrent to someone "falling in".

Over the past 15 years, it has served as a great vehicle for saving money due to its automated nature.

Admittedly, our internal thought process has been a bit more subjective in nature and is only being shared here privately with fellow investors in the context of helping us screen tenants to place in our first rental unit. 

Depends largely on the area, and sometimes the nature of the shingle.