I definitely prefer to do my own maintenance wherever possible but there are some tasks that I would prefer to farm out to a professional. For me, it is the detail work like drywall mudding that I prefer to hire out. It isn't that the task is beyond me, but rather that a professional can do it a lot faster. The other time I will hire someone is when the tools needed are not in my toolbox and I don't want to outlay the cash for a one use tool. Where do you draw the line between saving money and doing it yourself and paying extra to have it done for you?
I'm home doing nothing on Saturdays and Sundays so if anything is broken and I think I can fix it, I'll give it a try and wouldn't consider any time spent on that [even if I don't get the desired results] wasted. If I am unable to get the job done then I will call an expert but as noted, that's after I've given it my all and failed. For someone who's stuff is given to breaking down frequently, I'd recommend learning how to do the job yourself so that in future you can do all repairs and maintenance yourself in your free time.
I love doing DIYs around the house especially if its artsy stuff. I know my capabilities and if I think I can do it on my own then I'm going to do it my way and hiring someone to do and decide for me is a waste of time and money because i'll probably meddle around anyway. I also know my limitations, so if I think I cannot handle it on my own then I have no problem hiring someone to do it for me.