Dumb questions?

I have an Oddysey amp and Nestorovic speakers. The speakers have a 5-way binding post and the amp doesn't. I want to use the holes drilled into the post of both to connect new speaker cables. The hole in the amp post is about twice as large as the hole on the speaker post. I think about an 1/8" diameter for the speaker, close to 1/4" hole for the amp.(I'm not home right now) First, do I have to use a pin connector or can you put banana plugs in these holes? The hole for the speakers are too small to put bare wire through. Right now I'm using spades but I have to put one fork of the spade through the hole in the amp post because the diameter is too big to fit the whole spade around. Second, would the dealer I buy new cables from put these connectors on the cable for me as I don't know how? 3rd, any opinion on what type of connector gives the best signal transfer? (I find it difficult to tighten down spades enough) Thanks.
Mezmo covered just about everything here. I'll just add a couple of things.

On the bare wire vs. connectors issue - if your wire is silver or silver plated, bare wire doesn't really have any drawbacks. Silver will tarnish, but silver oxide has the same electrical properties as silver. Copper oxide can severely hamper the conductivity of your cables. A simple answer is for silver wire, just go bare, and for copper, have your dealer re-terminate them.

For bare wire, make sure to take extra care when hooking the speakers up to ensure that the wires on each post do not touch.

As for spade vs banana plugs, generally, a simple spade make a better connection than a generic banana plug, but there are some bananas that are excellent. The same can be said for the security of the connection. Most banana plugs are non-locking and will slip out easily. A good cheap banana connector is the Multi-Contact LS4. They're really cheap (about $2.50 a piece) and are much better for signal transfer than most other generic bananas.

Good luck.
So, it seems two spades of different sizes would work well because of the difference in diameter of the amp and speaker posts. I guess they do have wrenches specifically for stereo connections, right? Any opinion on whether I could or should use different size pin connectors in the holes? I really don't care for bare wire so I'm going to go with spades or pins. Thanks a lot.
I'd be careful when using wrenches, besides scuffing the posts and possibly devaluing the resale value, you might strip the posts. A tight connection is absolutely needed, hand tightening usually works. I have an old plastic "Postmaster" specifically made for this, but I understand they changed the design some years ago, and added a metal insert, which made it more likely to cause similar damage as a wrench might. I don't know if either version is still available. You can use a wrench, but do so with caution.
Don't damage the Nestorovic speaker posts. The driver has to be removed to replace the post...and the drivers are glued in...a major job. Spade on one or even maggie pins work on the other. Jallen Po