How much would be involved in sticking in a metal window well?

An excellent idea. Otherwise, over time, the soil will collapse in on the hole. However, you should dig down at least another foot below the window, fit in a well and fill the hole with gravel. That will give any water that does go into the well a place to disperse.

You should attach the well to the house foundation. Just use masonry bits and plastic or lead anchors. If you don't attach it to the house, soil and excess water will leak in between the metal well and the house.

If you truly can't use a drill and work bothers you, forget it, relax, have another beer!

I'm Amish, so I'd be using an eggbeater drill...

Just kidding.

The digging doesn't bother me. I'm a little scared of the prospect of messing with the foundation...worried part of the old foundation would crumble or leak. I also question whether any drill I have access to have enough oomph to get through concrete. What are the anchors called? What size would they be?

Use concrete screws--the most popular brand is Tapcon. You'll need a hammer drill. For the few holes you're doing, a 3/8" drill or drill/driver will do the job. And to make the whole job easier, you can probably get by with 6"-8" of gravel rather than a foot.

Don't forget to use a masonry bit, when drilling into any masonry