That's not going to happen until the bootloader is cracked (much different than root) - but for many technical reasons, the chances of that happenening are relatively low.
If the OP is a tinkerer, he/she probably made the right decision, the DROID is going to get to a point where it's very hard to find, and since it's out of production and somewhat "collectable", prices on eBay will probably end up skyrocketing.
I actually got tired of flashing ROMs on my Droid. You flash one then you find yourself waiting for a better build and it becomes a never ending anxiety for new ROMs. And none of them are/were even as stable as my DX is at stock. Hell, I don't even care about rooting my DX because it's so fast already out of the box.