There's not much in the industry that is disapointing to our business personally. I feel bad for so many people attempting to start out in the business and think that it's an easy task, realize that it's not and then end up "dumping" clients or abandoning them. The issue then becomes that the client doesn't trust ANY host. The good thing is that after they've hosted with us a few days (or weeks) they see we're a TOTALLY different type of operation.
Vacations are the only thing that I miss. I rarely get to take off 100% as I'm always around on call for employees etc, but those times that I DO get to leave, coming back after a week I always dread what type of mess will be left. Thankfully, it's never that bad.
So the only other thing that I don't look forward to are exploits in software. Many customers believe that since the software is operating on our servers, that WE should be the ones to make the updates, and don't understand the concept between designer, programmer and hosting company. We ONLY deal with hosting - everything else is referred to other companies.
As previously said - do what you love
I've been doing this since 1994. I'm still doing it
There is a LOT of freedom in this business.