@jpreisser89
Ok, what system are you playing on? PC, Mac or one of the consoles? And if on PC or Mac, are you using mods and/CC? And are you playing on a laptop or desktop?
I play on a PC desktop. My recent experience a couple of days ago with moving sims between households using the ask or invite to join household options is that there is a long delay between the time you do the social and the sim selection screen comes up to pick the sims to move, then another long delay before the move happens. But it does happen, and the sims do move where you want them to. Both delays are long enough that I thought the game was locked up and I getting ready to force quit the game when the selection panel finally appeared. That was the first time I've tried the move in option in ages, literally years, and I only did it to see if the issue that I had before with the moving sims inventories becoming unowned was still a thing. What I got out of it was the first move was incredibly slow but the second one I did was a lot faster. It probably took half the time the first one did. I only did the 2 moves.
So, I can tell you that it is one of the slowest things that happens in the game. It does work but it isn't instant by any means. Even the move that took less time took nearly 2 minutes which can seem like an eternity. The first was probably in the range of 4-5 minutes. My guess is that you might not have waited long enough for the move process to execute before force closing.
But the thing is, once the inventory issues started, I stopped using the live mode move options and just moved the sims via Manage Households. That avoids the inventory issues and goes a lot faster even though you have to exit the lot, go to Manage Household and use the split and move options there. That works pretty much flawlessly every time, at least for me. So, if you continue to have trouble with the live mode move options, using Manage Households is the work around to use. The only drawback is using Manage Households does not work to get your sim into a University Housing venue. Those sims have to use the live mode system to enroll and move if you want the sim in that specific venue. The workaround for that is to change the University Housing venue to a regular Residential or Apartment Residential (NOT a Residential Rental) so you can play on the lot. You do lose some gameplay that is unique to the UH venue though.
Hope this helps.