@Jeff Zimmerman   will look around those areas (online for now) and see if anything makes sense to look at.

They buy certificates online after a 30-minute "session" and a swipe of the credit card.

It's rare, but occasionally you can find a value add play where you'd be buying into a property with much lower than market rents where you have to do a renovation in order to get higher rents, and then you can get the 1% rule.

I've talked to a few people about doing rentals and most of their responses are about the same "start of with a cheaper small house, rent it out and gradually work towards getting more lots and then work bigger towards dupleces and so on" I need direction for learning tools I really am starting fresh, I don't have knowledge really at all on market what factors that are in play when going to buy a house or renting it out or anything like that.

Could be a factor at play.

 We use buildium property managment software which allows tenants to set up online rent payment via ACH.

I've been searching online for real estate agents and property managers, and it is so hard to know whether someone is actually any good. 

Also being awakened by them has been spectacular - nothing beats being jarred awake at 6:15am by a toddlers screaming at the top of their lungs horse playing in the front yard.

I used to play a lot of pool (billiards) when I was young. 

Small details make a small difference in the effectiveness of a marketing campaign.You don't tune an instrument that you are not playing.