Fourth, tenants tend to “try more stuff” with mom and pop landlords than property managers.

We don't know you, we have no idea how you act under pressure, how much hair a sec8 tenant will have you pulling out or how thick you skin is.

At one point he was flying on helicopters doing GI joe stuff, I found that fascinating and I developed a great amount of respect for him through this time while we were working together. 

If you don't, that's fine too.Real estate presents options for more time, more hands-on, gnarlier stuff. 

I do my own transactions, not that hard anymore with a good escrow company and all the docusign stuff..... 

Life's just too short for dealing with stuff without having all those professionals and that economy of scale between you and the tenants.

People have a good time doing stuff is always a good thing.

I would be able to manage the finances, marketing and showings even while working but maybe not attend to the small stuff such as getting a random call to fix something stupid at 3pm when I'm 6 hours out of town or on my 30th day of night shift 12s. 

Since you are not a skier, a home or cabin that is close with its own hot tub and other stuff sounds great You can do much more with a home than a condo.

Don’t skip safety stuff either—make sure you’ve got working smoke detectors, fire extinguishers, and a first aid kit.