Since you said he has enough to live on no matter what he does, I think he should choose the course that causes him the least anxiety.

At some point, the aggravation and anxiety just isn't worth it to me anymore.

Though Central Austin is can be a very lucrative location to invest, purchasing properties there come with a premium and lots of competition, maybe researching and investing in areas that are more affordable could lessen the anxiety of starting out.The links to building your foundation is good idea as mention by @PaulTimmins above.

This uncertainty can cause you great stress and anxiety - you only get your check after your property sells.

If you want to change your experience in real estate investing from one of anxiety, frustration and disappointment to working less and making more, you'll make the change.

This property has a vacant lot attached to it (multifolio) which I figured on selling along with a stand alone 4/2 that is adjacent to it to get some of my capital back and then finance the rest of the buildings with that 10 year . so many moving parts though it gives me a little anxiety.

My nerves & anxiety has slowed our progress in the real estate market. 

@Nicole H.im in process of purchasing a 4 family home through the program...i just needed a second oppinion,because i dont know anyone else who have heard from them.You just calmed my anxiety,lol thank you!

How do you handle your anxiety at your monthly in-person meetups?

Definitely settled some of my anxiety regarding leaving investments in the hand of property management.