Buying your first deal is the toughest because there is a mental obstacle to overcome.

However, some individuals have the mentality that everyone in the world is trying to get an upper hand on them and they refuse to even have a conversation- which i find wildly strange. 

If you can provide some clarity on those then the community can give you some better guidance.

A 3 hour driving radius will give me a good mix of interacting with guests ( greeting them at check-in), driving by simply to check on the condition of the house, and also having a hands off mentality.

Get some clarity.

It's easier to keep the 'it's just business' mentality when you havent blurred the lines before. 

YNAB does push people to prioritize money/goals and enable them to set money aside which enables them to achieve their goals much faster due to this clarity and focus.Case in point, I just had a friend who has been using Mint.com to track expenses for the past 1.5 years and just switched to YNAB in the last 2 months.

Certainly can dive into this deeper for you, but need clarity to best answer my friend.

If so, that will provide you more clarity. 

Most start charging what their employer charges because people use the mentality of I can do this on my own to make the same money.