360 Advice Needed - Autocross / Street Engine Build

Is cutting the pistons a possibility? How much needed, is there enough meat?
If the engine is together, that would be a pain. .005" removes about a 1 cc. So getting 5 cc's out would require a .025" cut. It is an option I would certainly consider..... but would need measuring the domes as noted.

Oil pan would be the milodon. It's a tight fit. What Kmember are you running? But hard to put on a fit with motor in car. Protects motor investment. Also not cheap.
If the OP if gonna pull some cornering G's, THIS is good advice. IMHO, the OP should spend some time reading up on pan baffles, one way doors, etc.

I'm late to this show, and I think autoXcuda's input is better than what mine would be anyway. But, I can comment on this cam if it's still a consideration. I run that lunati 60404 in my 340, which is a .060" over '68 340. Compression is 9.8:1 with the KB 243's .018" over the deck. Heads are iron 308's, chambers are 65cc's, 2.02/1.60 valves, stage II ported and flowing 264 cfm @ .500". I run it with a eddy air gap, holley ultra 750 double pumper, doug's headers, and currently have it in front of an 833 with a 3.09 first gear, 26" tall tires and 3.55's.

Idle for the street is getting a little borderline, it only pulls about 11-12" of vacuum at idle, which is around 750 rpm. I had to play with my timing to run California 91 octane, I'm at 22* initial but I run heavy springs in my distributor and my total is limited to 32* all in mechanical. Advertised power range is 2200-6400, and that's the truth. It does not like to pull below 2200. And really it's not happy until its at 3k if you're going to stomp on it. Past 3,500 it will push you back in the seats hard, and it goes from 3,500 to 6k in a heartbeat.

Overall, it's a big cam for the street. For the daily driving I do it can be a bit of a pain. On the track you'd want to keep it at 3k or higher, stall is supposed to be 2800 or more. The 3.55's are smaller than what the cam wants, my plan is 4.30's and a T56 to keep the top end speeds, but still have 2 gear with the revs up for autoX. Here's the idle

***Edit***
Here's the compression and DCR info for it, as I said I've had to pull timing to manage this for 91 octane
View attachment 1715100326
Nice comprehensive post, blu. FWIW, the lower 500 RPM performance on this cam's advertised RPM range is not too surprising.... I find that most cam mfr's including Lunati and Comp, push the lower RPM limits down too far, so they look better on paper. Crane's RPM range numbers to be more conservative and more reliable.

That 91 octane sure is more of a problem than I expected. OP, what is the source of 94 octane out there?

I think at 5500 rpm up sustained you are going to get some loss of lift and/or valve float. The weak link to RPM is usually valveteain before bottom end.
And that may point to a milder ramp cam. Or the solid lifters; they will avoid the pump-up problem but then there may be increased lifter weight added to the valvetrain weight.