So as a first step, we invited out an electrician to see how much wattage we'd need and how much it would cost for them to put in a transfer switch. I'd just like to say that if I could earn $500 an hour as an electrician, I think I'm wasting my time working in IT. That is insane. And that cost is including a ridiculous markup on the 2 tiny parts they'd be supplying (not the box or the generator, those have to be purchased separately). At least he gave us a decent estimate on what kind of wattage we're looking at.
After asking around a bit, it seems that the electrical work is almost as easy as adding a new light. We'll need to poke a hole in the siding for a plug for the generator, but that's pretty easy and a much better option than leaving the window open for the cord. So we're going to attempt this ourselves. And with all that money saved, we'll, um, have less debt.
But this is going to be an interesting process. The electrical box arrived yesterday, and I'm hoping to order the generator today. The one I'd originally ordered is back-ordered 10-12 weeks. Which doesn't really do a lot of good, seeing as the instance of power outages over the summer is pretty light.