elmariachi Jim I missed the Dallas thing unless it was Football. Anyway, Couple of things here are not quite right
Pressure plate bolts rely on the first 3-4 thread for 90% of there holding powers on a clutch pressure plate to flywheel.
I have run an iron flywheel (40#) for 3 years and now run an Aluminium one. There are helicoils in the Summit one I have. Yours may also have them or a timesert for the clamping power needed. I have not had a pressure plate bolt come loose in any of my cars or the Vettes, GTO's, or trucks I have worked on in the last 10+ years. I allways used Loctite for flywheel and pressure plate bolts, RED not blue. You are worried about your bolts in your clutch, you should see the small ones now being used in the new stuff. 8 & 10MM heads on a 1/4" -5/16's thread.
If you are running a RACE clutch with a 3,800# and up clamping load and up I could see the issue with longer bolts. Most Cobras are running a 2,800# to 3,200# on the street. If you want more holding power of a clutch, multi disc is the way we are going.
I use the washer on my bolts and have no problem. I the old days there was a steel ring that the bolts of the flywheel went through to not gall the surface of the flywheel. I never found loose bolts on one of these motors with 20-50 thousand HARD miles.
There is alot of heat and expansion going on in the bell housing, also alot of stress on the pressure plate bolts. Having washer washers spreads out the load bearing on the heads of the bolts, they may even absorb some of the loading and unloading pressures. I believe in ARP bolts, nuts, washers, and other fasteners. I have used them on motors for more than 30+ years. I have broken everything in a block but have yet to have a bolt break of theirs cause the main failure.
Jim go with a longer bolt if you want, just make 100% sure that the other end doesn't hit the block, or block plate in a full 360 degree rotation. I have seen this happen a couple of times.
Rick L