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I've done it, front and back, and I had one that took about six tries before I could get seated just right. I don't have any great advise, just take the thing all the way off and try again.
I've also done it. The rebuild kits are about $15 from Fred Beans. Getting the boot on the first piston and seated in the cylinder took me about an hour. After that, I seemed to get the hang of it (I wish I could remember what it was). Here's a link if you don't already have it. http://www.installuniversity.com/ins...er_rebuild.htm
It all boils down to Time & Convenience VS. Money...
The rebuild kits are very inexpensive, four kits will be around $50 from Chevrolet,
I thought about it .... laughed about it AND
forgot about it!!! ....when I came across a set of four brand new red Delco ZO6 calipers for around $300..
My car had almost 70K at the time, I just 'bite the bullet" and bought all new rotors and calipers. It was fine, except for the fact that I sold the car less than a year later!!!
As the others have mentioned it is fairly easy to do. One caution. You need some air pressure to get the pistons out. Follow this advice from the Service Manual:
Remove the brake caliper pistons from the caliper bore by directing low pressure compressed air into the caliper bore through the fluid inlet hole.
Caution
Do not place your fingers in front of the piston in order to catch or protect the piston while applying compressed air. This could result in serious injury.
Notice
Use clean cloths to pad interior of caliper housing during piston removal. Use just enough air to ease the pistons out of the bores. If the pistons are blown out, even with the padding provided, they may be damaged.
I bought four new ones, disassembled and had them powder coated to Mag Red II. As stated, disassembly took some pressure to get the piston to come out. I used a block of wood with a rag on it so that with each blow of air the piston would only move about 1/4". Then I would change the block of wood for a thinner one and move the piston again. I did this until the pistons were about out and then they came out by hand.
For rebuild, I put in the seal and then the outer boot engaged in the piston stretched into the caliper. Engage the caliper and then push the piston in. As you do the boot collapses nicely. The GM kit also comes with a special grease for re-assembly that makes it much easier. If you do decide the rebuild them, get the GM kit as it has all the parts and the fit is perfect.
IMO only get the re-build if you have torn boots or damaged seals. Otherwise it will not really buy you much, and its not any easier than what I assume you are doing now. Next time I have a "issue" I'm going to get new calipers.