is this seedling ready to be planted?

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as you might be able to make out from the stainless ruler, the stalks are about 4" tall. Love the foliage! It's very healthy!

Anyway, it's almost fall and the temperature is going down and the days are getting shorter. I'm wondering when would be a good time for me to transplant. Now or should I wait for spring? Maybe if I wait for spring, I should give it a much bigger pot to keep from getting the tap roots bound all up.

thoughts?

First of all, what kind of plant is that? From the looks of the leaves, I will guess that it is some variety of Holly. If it is a Holly, then (depending on the species) you'd probably be fine to transplant it to it's eventual location in the ground. A lot of Hollies are very hardy. And most shrubs and trees are best planted in the fall, when they go into dormancy, so that they get established over the Winter and are ready to do lots of growing in the Spring.

If you don't plant it out now, then get a pot about twice as big and put it there until March.

Best of luck!

Oak

ok, good. plant it out now.

it'll survive the winter?

Oaks can be either deciduous or evergreen. I'm not sure but looking at the leaves that looks like a white oak/hybrid. Have a look at the wiki page.
http://en.wikipedia.org/wiki/Oak

I think it is diseases that you have to look out for the most. I'm no expert though.

In any even you are going to have to plaint it at some point. Do you have a large garden?

Sure, oaks are hardy.
Fall is actually a good time to plant many trees, as they get established during the winter, and then are ready for new growth in the Spring.
If you plant it now, make sure you water it regularly until it gets cold, then hold off until the weather warms up again. Should be pretty easy.