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