Sorry for the long background...After moving out of Florida, I realized that I can't fully use my iphone 8 plus while wearing gloves, a problem that never occurred to me living in south FL. Essentially, even with touch-enabled gloves, you can't use the home button because activating the home button requires contact with skin. One partial workaround is to swipe right while the phone is locked, and click a recently used app from the menu that pops up. This enables you to use the keypad to unlock the phone instead of the fingerprint, and touch-enabled gloves work on the keypad. However, once you're in the phone, there's still no way to navigate back to the home screen if you're wearing gloves. As someone who is outdoors a lot, this has become a problem in the winter, obviously, and a big problem in the back-country when I check my GPS app frequently. I do a lot of winter backpacking trips and this becomes very annoying in sub-freezing temps. My phone is in excellent condition and currently worth about $300 on eBay. I've never been a fan of upgrading to a new phone simply for the sake of having the newest gadget (hence why I still have the 8 plus), but there are material advantages here: iphone 11 pro has legit battery performance, about 5 hours more battery than my 8 plus 11 pro has a truly great camera (I take a lot of video/photos on my backpacking trips, would be nice to have something to work alongside my Canon m50) I can actually use the phone in cold weather while wearing gloves I can afford a new phone, but being somewhat frugal I'm hesitant to spend the money. Then I got to thinking, could I be at a disadvantage by waiting till a time when 8 plus might only be worth $100 or less on the used market? In other words, if I'm going to upgrade in say the next 18 months - two years, it could theoretically make more financial sense to do it now because my phone is worth ~$200 more than it will be in the future. Based on historical pricing, it's unlikely that the price of the iphone 11 pro will drop by $200 in the next 24 months. When do you upgrade?