360 Advice Needed - Autocross / Street Engine Build

Thanks to all you guys for jumping in to help, this is exactly why I'm asking the questions at this stage.
It's seems that I have some mis-matches in this setup, if I understand correctly:

1.) DCR is generally too high for 91 pump gas: Baseline @ 8.8:1 , goal would be to reach under 8.2:1
Possible solutions with current bottom end:
- Increase cc's of cylinder heads (I think some CNC prepped edelbrock heads are 68cc's, drops DCR to 8.3:1)
- Increase head gasket thickness (0.054" gasket would drop it to 8.4:1, but quench height would become 0.049")
- Increase cam duration from 275 to 284 (only lowers to 8.7:1)
or a combination of the above???

2.) Gear ratio / high stall converter:
- Seems like 3.55 gears with a 2500 stall would be an ideal compromise here.
- Alternative might be to keep the 3.91's, but put in the stock 11" converter.
A bit slower off the line, but the gearing puts me at about 5600rpm at 110 mph, and backroad cruise of 2000rpm at 40mph

3.) Manifolds:
- I'd like to look of it being mostly factory, and the lack of headaches that seem to come with headers.
- That said, if this thing is going to die off after 4500-5000 rpm, or have heat issues from choking that off, I may need to change.
- Headers would need to be shorty style, any suggestions who makes a good pair for the a-bodies?

4.) Oiling issues?
- I have a windage tray, and a high volume pump.
- Other than that, the oiling system is stock and I haven't considered it much.
What did you end up doing to keep it picking up oil at the track?


Thanks,

Ryan

Is cutting the pistons a possibility? How much needed, is there enough meat?

Only shorties I would bother with are TTI's. Not as tricky to install in car as oil
pan. They are expensive.

Do you have HiPo cast manifolds?

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.