Now that 2019 is done, here's my top several items. Most of them this year are super cheap, silly looking things that have brought me outsized use or joy:
Google Mini Outlet Mount: I had several google minis from a year or two ago when you could basically get them for <$10 or free and never used them. But I realized I was always turning my UE Blast speaker on in the bathroom to listen to music while I showered, and it was a little finicky to get it to connect right each time (sometimes it would preferentially pair with my wife's phone). So I bought this thing and mounted one of the minis in the bathroom. Awesome upgrade and don't need to mess with the bluetooth speaker for this anymore.
Smart Powerstrip / Surge protector: bought on a lightning deal for $2x and allowed us to put our bedside lamps on voice control via alexa. These were the only lights that were still 'dumb' and a quick fix.
Shoe stretchers: Did not really expect this to work but for <$20 I figured I'd give them a shot. Bought a pair of final sale cole haan sneakers that were too small for me. I could wear them for about an hour before I needed to take them off. They now fit perfectly after about a week of progressive stretching.
Toothpaste corkscrew: Really struggled to buy this but I figured it wasn't a super passive aggressive way to get my wife to squeeze the toothpaste from the bottom rather than the middle, and put the cap back on. She loves it, we gave the other 2 as presents to her parents and mine, and as a bonus it makes tubes stand up on the vanity.
Tongue Scraper upgrade: I think this is the original thing I posted ITT and I've tried several different versions. The plastic ones I originally posted can be too harsh, and the Dr. Tung one posted afterward is excellent, but the rubber handles get gross. These stainless ones are just as good as the Tung one, but they don't get moldy, and they can easily go in the dishwasher if you want to sterilize them. I keep one at work, one at home, and one in my toiletry bag