Nothin wrong with that. There's a progression, and eventually it won't seem as daunting. BUT, meantime, you're keeping an old truck on the road, so it's all good. Brakes are a good place to start when you need to. They're easy enough to get to, there's really only one way (please don't prove me wrong) to take them off and put them back on, and it's ~$100 in parts that would be a $300 job for a mechanic to do. Couple hours, some crud under your nails, and it's all buttoned back up.
I've done a lot of different random stuff over the years- still haven't wanted to crack into the timing belt. For me now it's more "do I have time for this, and/or do I have time to have the truck down a while while I scratch my head over this repair?" So I'm kinda 50/50 on hiring stuff out.