Doing it yourself vs paying someone. Lemme tell ya what I have done to bring myself up to speed. 1997, I got into a hosting biz myself, but my first experience was a RaQ and it was a pain, I knew nothing about it, my but host was nice enough to take care of things for me, till I ended up having to get a second account with another company and it was a pain. Having someone around to take care of it for you is great, but when a time comes you need to do something.... your screwed unless you have good search capabilities. Anyway I got out of it two years later, and wanted to get back into it when I had better finances. But I needed to brush up on my experiences, so I took remote jobs with companies, forcing myself to re-learn it all over again. Now I dont have to rely on anyone to take care of my needs. And if and when I have someone around, Ill know if their actually doing work, or goofing off. If I make mistakes, I know I did it and no one elses fault.
When it comes to someone else, you must have some sort of trust. Although theres the professional courtesy, but you never know who you are going to get if you hire someone you dont know to manage your servers. You have no idea the kind of work you will recieve for the amount you pay in return. All depends on what you feel is best.
But Ive learned experience is your best teacher. IF you want it done right, its best you do it yourself

Unless you are agood person to work with and have found someone who is good to work with to, vice/versa develope a nice relationship and it could take off. Then again, if their out of town, on business or have something to take care and you have no one else and something goes wrong (believe me you never know when something can come up) your up the creek with no paddles.