I've got a 10.25:1 C.R. on my 103 (was 96). Compression releases are necessary. I'm running the stock starter as my H-D shop said the high-torque starters will eventually tear up the ring gear. 31k miles and zero troubles.
I have SE 10.25:1 cast domes in my 95" 2000. No comp releases, no headwork.
Should have done CR's, though I get by just giving the starter a quick bump, then starting the bike.
The kit came with fitted pistons which are cast, high compression type domed. The kit included new cylinder, gaskets and rings.
You didn't' mention any cams. I hope your not going to try and run the 26's with that kind of compression. If your going to run over 10.1 comp you will also need to choose a cam that's right for your application as well, this will help bleed off some of that comp. A SE 211 or a S&S 570 comes to mind.
The 211 will require no headwork but the 570 will.
krusen--I appreciate thrift, but you ought to wait until you have a plan for a build that takes into account tuner, exhaust, intake, heads, etc. If you do great; but, if you don't you are doing a "science project" as a friend of mine, who is in the HD performance business, refers to cobbling together a bunch of parts.
I bought a big bore kit that includes new cylinders and fitted pistons. 10.1.25 compression.
The Big Bore kit said it is a straight bolt on and is made at V-Twin Manufacturing. Does any have experience with V-Twin? Any Dvise would be very helpful. Thanks guys
Your best source of advice is V-Twin. Have you bought a kit for installing on a stock TC88 bike, or did you specify that you were going to be using later spec TC96 heads? If it is for a stock engine I don't see a problem!