Does this set up require a stronger battery or higher output starter? I'm a little concerned because it already acts like the starter is a little weak sometimes. My Evo fired up with less effort for sure. Thanks
If the starter is acting a little weak it may be a compensator problem, the stock compensator in the 96 inch and earlier 103 engines are junk.
My 08 has over 100,000 miles and it is still on the same starter that's been in the since the bike had 16,000 miles, the reason the starter got changed was because the bike had starting issues and the dealer swapped it out on warranty but the real problem was the compensator which was repaired later on and fixed all my starting issues. Also my bike was running a 103 Big Bore kit for 5 or 6 years with no compression releases and I never had any starting issues, so NO you don't really need compression releases.
I run the SE 255 cam and I switched to the Woods TW222 cam and I was much more happier with the Woods cam over the SE 255 cam, I never run a Andrews cam in my bike.
Also if you are doing the work which it sounds like you are going to do I would consider putting in a 103, 106 S&S or a 107 Big Bore kit. The 103 would be cheapest if you call PC Pain (Jon) at Horny Toad HD and tell him you're a forum member you will receive a discount on parts, brand new 103 cylinders are only around $250 and piston and rings are not too much either but I can't remember the cost but you can do the 103 BB for around $500, with a cam, cam bearings, lifters and adjustable push rods you can do the engine upgrade for around $1000. Also your bike has the "B" lifters in it and they are pretty dependable lifters so if you don't have many miles on the bike just reuse the OEM lifters and just do the adjustable push rods, going this way you can cut cost and it is easy to change the lifters later on if you need to.
The only specialty tools you need is a cam bearing installation/removal tool other then that torque wrenches and basic hand tools will do the job, and you can use a 4 inch hose clamp as a ring compressor.