Obviously you can do whatever you want, but if it was me....
I'd use the plug wires I already have with a small cap. I run a small cap on my car as I plan to go 2x4 carbs sometime in the near future and the large cap wouldn't fit. Whenever you need to change plug wires, go with the MSD 8.5mm. (I currently run the 8.5MSD wires and I like them a lot). I tried out cheaper wires and the problem I ran into every time was that they'd break when I'd try to disconnect them from the plug. I've got a new set of msd wires and one that I bought in 2005 and they still test perfectly.
If you wanted the large cap, you'd need new wires ($80) and the adapter (Cheapest at Rock auto for $3, put in a 1988 F150 with a 351 and go to the ignition section, they have cap adapters, and don't worry, you CAN paint the adapter and distributor cap).
On my truck I run the large cap:
http://www.summitracing.com/parts/msd-5504/overview/On my car I run the small cap:
http://www.summitracing.com/parts/msd-5506On paper at least, the large cap is probably better..... but better is relative. This car never sees over 5,500 rpms and my truck never sees over 4,500 rpms. At these levels I highly doubt it matters, and although I have no dyno to confirm or deny my feelings on this, I *suspect* it makes no difference as long as the parts are good quality.
It's kinda like asking yourself, "Do I want 150% overkill or 165% overkill?"
I don't really know anything about Edelbrock carburetors, but i suspect the issue is that the drop base was designed for a Holley 4150 style carb with it's fuel attachments. I run a Holley 4010 on my truck and I had to be really picky with what filter base I used because of the same problem you are having. Luckily in my truck, there is an absurd amount of clearance, even with a 2inch carb spacer

Not so lucky in the Galaxie.
Running about the same compression you do, with roughly the same ignition (duraspark dizzt, msd box) I run these plugs:
http://www.summitracing.com/parts/ngk-2227/overview/ Wes Adams suggested them to me, and they've worked out just fine.