Ok so i've been doing some research and getting some prices. It seems no place wants to install a full set of wheels without the tire pressure monitoring system (tpms) in place. Apparently they cost about $60/each, and you have to program them into your car's computer. So my options at this point, from worst to best:
1. Buy winter tires and have them mount them on my current wheels, and just pay to switch them every time. This is a shitty option because it requires me to make an appointment to take my car in twice a year and I have to pay to swap the tires, and also pay to reregister the tpms to the car. Every time. Every single person I talked to recommended this option (because they want me to pay them now, then twice every year!), even after I explained my entire purpose was to save myself money in the long run and just swap tires myself. Initial expense of about $900 (for 2 new sets of tires), and about $200/year to constantly switch them out.
2. Buy a new set of winter wheels, plus $240 worth of tpms. I still have to pay the dealer or tire service center to reregister the tpms twice a year. Unacceptable. Initial cost of about $1350, and about $100-200 recurring cost every year.
3. Buy new set of winter wheels with tpms, and buy the tool to register them myself. This has the advantage of never needing to go into a service center, but the disadvantage of purchasing a $150 tool upfront and learning how to register my tpms myself. This option will cost me close to $1500 upfront, with no recurring cost.
4. Buy new set of rims without tpms installed. I don't know if this is an option purchasing from a brick and mortar store. I didn't ask specifically, but many sources online indicate they can't legally install a tire without tpms on newer (2007+) models. I don't know if that's applicable in my state or not. It seems like I can order a set online without it though (although I didn't actually go through the order process, just put it in my cart to get a total price). This option will still cost me about $1100, but I will have no recurring costs. Of course I won't have a tpms with my winter tires on either.
5. Get new wheels with cloneable tpms. This way no reprogramming of the car is needed. You just clone the 4 IDs of the current tires, and reprogram the new wheels with the same sensor IDs, then when you swap sets your car can't tell the difference and reads the same set of sensor IDs. This will probably cost around $1500 total, and I will have to pay the service center to clone the new tpms IDs for me, but then I should be all set from that point forward.
I think option #5 is the clear winner if possible. I am hoping I can take the car in and have new tires put on in the next week, and get them to give me the current tpms IDs, then in the next month or so I can order my new wheels/winter tires online, and hopefully have whoever I order them from preprogram my cloned IDs before they ship them. Then I could just slap those babies on as soon as they arrive and have a fully functional tpms.