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.
OK, first of all, love these questions -- and nothing dumb about them.

The hole drilled laterally through the post on the speaker connecter is really for bare wire. Thread the wire through the hole, and then tighten down on it. You don't need to use the hole for bare wire, however, (you can just wrap it around the post and then tighten down on that), but as far as I am concerned, that's the only thing that that particular hole is good for. Thus, if that particular hole is too small for the guage of bare wire you have in mind, you can still use bare wire, you just have to avoid the hole.

If you want to use spades, you'll need a spade large enough to accomodate the width of the post. Sounds like you've got posts of materially different widths, so, you can terminate with different sized spade terminations. You don't really want to thread 1/2 of a spade termination through the center hole in a post as -- as you've discovered -- you really can't tighten the screw on it without damaging things.

Bananna plugs do not go in the hole drilled through the side of the post. You don't want to put them there. Rather, they go straight into the end of the post. To use a bananna plug, in other words, the post needs to be hollow -- and it's into that hollow end of the post that the bananna plug goes.

So, I guess in an effort to recap, you can always use bare wire. Wrap it, thread it, what have you, tighten it up and squash it down, and you'll have a pretty damn good connection. The hole drilled laterally through a binding post will assist in this quest, but it is by no means necessary. If you're looking for terminated wires, sounds like you may need asymetric terminations (just made that up -- but, basically, something different on the amp end than on the speaker end. This is quite easily done.) You could go with different sized spade connecters. You could go with spades of the appropriate size on one end, and bananna's on the other. You could use banannas on both (although it is not clear that the amp-end is designed to accept banannas). You get the idea.

All things equal, some say that bare wire is the best connector -- as there is a whole lot of smashed up contact area for signal transfer and no intervening mechanical connections with the potential to fail. Others will say that bare wire leaves open potential vectors for oxidation that will degrade the signal over time, whereas a solderd connection to a gold-plated termination eliminates the oxidation factor. Each true, so you takes your pick and goes with it.

Finally, depending on the wire you go with, and where you get it, you should be able to acquire any old configuration of termination (or none at all) your heart desires. As long as you know what you want, any dealer you're talking to should be able to figure out how to make it happen. Helpful...?
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.