Reading through your cons, pretty much every con you listed can be resolved
You can, like you said, get a close friend to hold onto your bells and stuff for you! It may take a while to transfer all your money and what not over, but it's totally worth it. You can also find someone on TBT to hold onto your dreamies for you! You'd probably have to find multiple people to hold your dreamies though since you said you have 4, but yeah, you can basically use the TT'ing method to get your dreamies to move out, have someone from TBT take the dreamie to their town, and when you get your new town, they can get your dreamie to move out and then you can come and take them back. I held onto a dreamie for my friend for a while and she recently took him to her town as well, so it's reliable.
If you hate time-traveling, then yeah, you'll probably have to wait a bit to get all your progress on Main Street back. Me? I time traveled quite a bit and I'm already at the T.I.Y. despite restarting on the 3rd of this month. Plus, knowing what it is you need to do this time around to get the upgrades helps tremendously in actually obtaining those upgrades.
I say you go for it! Most people who reset don't regret it, at least from what I've seen. Just make sure you've got all your needs transferred over and what not.
