So this turned out to be an amazing trip - I'll recap below for posterity if anyone goes in the future....
Chile - Flew into Santiago and realized quickly there was little there to do. Our hotel was in Vina Del Mar which has to be among the most beautiful places on the planet. Pure blue ocean - everything on the beach. Had the opportunity to tour Valparaiso as well as Vina Del Mar is basically the same city. If you're looking to get away for a vacation in an off-the-beaten-path place, Vina Del Mar was majestic. The only crime to even remotely worry about was the "docks" in Valpo but keep walking and have a "No, gracias" loaded in your chamber when you get approached and you'll be fine.
Punta Arenas, Chile - the edge of the earth, the city sitting on the Strait of Magellan. The one thing I wasn't prepared for was the amount of street dogs. It was an ok city and a good jumping off point to one of the penguin colony islands (which was awesome) but there isn't much to do or see here for more than 2-3 hours. We even saw a dead street dog in the middle of a walking path which was depressing. If you go here, I highly recommend the Magdalena Island tour through any of their local companies to go to a penguin colony island with no civilization, just a walking path and penguins - it's about an hour long boat trip to get out there.
Ushuaia, Argentina - unfortunately due to the rough seas, our tour was canceled here - we got to eat at a great restaurant. Get the King Crab is all I can say and brush up on your Spanish because there are very few English speakers here. I'm fluent and didn't have a huge problem but it was a amazing to see that lack of English speakers in these countries - not because I expect the world to speak english, but because I've been to Europe a few times and was amazed at how many people also could speak English with no issues.
Falkland islands - the best part of the trip. It was a 3 hour boat ride out to the Falklands, a 3 hours OFF road drive to the destination, but the half hour we had there was amazing. there are 3 types of penguins on their island - you can touch them you are so close - stand next to them - etc etc, and it's the purest ocean I've ever seen. I have some pics I'll upload later. Be prepard to be off road for 6 hours of your tour. The ride out is VERY bumpy and unsettling but worth it when you get to your destination.
Buenos Aires - be careful. It wasn't a very friendly place if you're an american - especially the cab rides. Make sure your Spanish is near fluent before you go or prepare to never take a cab because it's a racket there. they'll usually wait until you get in, ask where you're going, then start driving an quote a ridiculous price that you can't understand. Even when we managed to find an Uber, the guy showed up drunk and demanded cash the entire trip - I guess, ask questions if you have them because overall the city is pretty beautiful - you just need to be sure you get around and stay safely. I proposed to my now fiance under fireworks on the La Mujer Bridge on New Years and that part made it amazing. Overall though, I disliked Buenos Aires - our tour guide made me feel unsafe at all times and to watch out for EVERYTHING. But Chile blew Buenos Aires away.