2.76 open to 3.55 Sure Grip...expectations too high?

Okie dokie, here are the results of the leak down test. The initial numbers were not exactly what I was expecting judging by the compression test, so I conducted two tests per cylinder in hopes of some consistency.

CYLINDER DROP IN PSI @ 90 LOCATION OF LEAK
1- 10, 12 OIL DIPSTICK TUBE
2- 6, 6 OIL DIPSTICK TUBE
3- 3, 5 OIL DIPSTICK TUBE
4- 4, 4 OIL DIPSTICK TUBE
5- 5, 6 OIL DIPSTICK TUBE, CARB (?)
6- 4, 4 OIL DIPSTICK TUBE
7- 3, 4 OIL DIPSTICK TUBE, CARB (?)
8- 2, 3 OIL DIPSTICK TUBE

I'm not sure why #7 was only showing 3 and 4 psi leakage when the compression was so much lower than the rest of the cylinders. I'm also wondering why numbers 1 and 2 are leaking so much more than the rest. Then I got to thinking, when I rebuilt the engine, I had trouble with the rings on those cylinders (in other words, I damaged the rings upon installation). I removed those pistons, replaced the rings, and checked for damage to the cylinder walls. I didn't see anything that I thought was major, nothing I could feel with my fingernail, so I proceeded.

Is it possible for air to leak into the crankcase through a loose intake gasket, or would that ONLY result in air leaking out through the carb?

I'm also not 100% sure I heard air leaking through the carb on numbers 5 and 7, my shop air leaks like a sonuvabish.

Exactly. Too much "rule of thumb" info given as blanket statements. What you posted is where I was heading in my post on page 1. After reading the interwebs so many believe it's the same as adding 100 hp. A basically stock 318 will notice a "little" difference at the 0-25 punch, but it's not earth shattering on this type of gear change. Now take a car that doesn't have a good converter and a big cam, yep, the jump in gears will do wonders.
I trust what you say, and it makes sense. I think after listening to the input here, I'm past the gear ratio "problem" and headed down the rabbit hole of "where is my engine losing efficiency?"

These are good lessons, because I need to learn diagnostics like checking compression, etc.