He's just like "I make $300K per year from my medical profession job, I'm going to make my life simple and aggressively pay down the mortgage, then do it one more time on another property, and that's it - early retirement." 

My Real Estate attorney always gives me advice and allows me to ask simple questions all the time.

I like to keep things simple.

For right now, we don't need any extensive features, but just want the software to be a little more user friendly and RentRedi seems to lack a few simple things that we would like in a property management software.

It is pretty simple. 

It’s simple, brief and the right pair doubles your money each transaction.

Adi,Real simple advice.  

Forget trying to walk them through a simple repair over the phone, to avoid sending a ServiceTech and saving an owner money.

I manage with simple notes, spread sheet, even just making tags in my phones SMS to search back and find that person every 30 days.   

I also have a world class designer on my team that helps get these kind of properties from the average $60-$75k/yr range to over $100k/yr range (for 3bd homes; more the bigger you go).