Originally Posted by 55/Rad
A lot of us started exactly the same way. Nowadays, I can't imagine anybody else working on my bikes.
Headsets are still left to the LBS but only because the tools are too expensive for how little they get used.
I bought tools indvidually as needed. Seemed smart at the time. But, if you know you are going to really dive in, I'd suggest a kit. Not a $400 set, but I've seen several in the $100 range that have most of what you'll need.
The only advice I'll offer is to be patient. You will make mistakes, but far less so if you aren't in a hurry. Some tasks take a bit of dexterity that only comes with practice and experience. Before long, you'll wonder why you ever thought differently.
And remember - good advice is easy to find right here and on the Parktool website.
Good luck.
55/Rad
A homemade headset press is about $3.