This looked intriguing, but I'm worried that YNAB is less user friendly for my situation.Queue the back story: I work as a realtor with a small RE investment portfolio, and my wife is a more stable W2 Engineer. 

Scratch & dent furniture & appliance outlets are your friends!

Like Brandon mentioned - you sound like the picture perfect classic "DSCR Loan" borrower - dscr loans are made for exactly this typically - LLC friendly and usually the best fit for when investors hit the 5 or so property mark and hit a roadblock with banks, cash etc like you desribed.Check out this 12-part article series published here on BP on all about DSCR Loans, hope it helps!

Friend How did you finance this deal?

Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.

We are looking to rent our primary house and move to a slightly bigger house in the same town because my kids do not want to leave their friends. 

It is my LLC to his LLC , a friend that Ive known for 9 years working many notes with ,not that close a friend.

I've had friends that lost all back rent to a property management company that went bankrupt. 

I have a friend who has vacation rentals in that area.  

The best advice on this topic, in my opinion, comes from 2 books:How to win friends and influence peopleNever eat aloneI am also looking for brokerages to work with or even experienced shadow / intern for to gain experience and additional knowledge.