It was comforting and reassuring knowing that I'm not alone or behind in my investing journey...""

Ultimately, it's about you and what works to give you enough comfort and protection from all the unknowns.  

This means providing top-notch customer service, keeping the place clean and comfortable, and adding thoughtful little extras.

Very comfortable with taxes, but haven’t done tax work for years, so sometimes I seek advice on things I’ve forgotten.No one is going to do the level analysis and planning that I do with my own taxes, so I’m fairly certain I’m saving a significant amount of money in legal tax avoidance. 

Buying out of state can seem a little out of your comfort zone at first until you see it can be managed.

and yes I have done the majority of the work myself and supervised the items I'm not as comfortable with.

Some days I am like this was 1000% worth it and others I am like how are people so comfortable with this!?

What I did was buy a single family home in the worst neighborhood you would feel comfortable moving your wife and kids to within 15 minutes of your home.

The sooner you start, the sooner you will feel more comfortable with the idea of investing in a property. 

Everyone has different comfort levels with their money, you should do what makes you comfortable.