If you're really anxious to get up there one last time this year (you are absolutely correct about the weather window, these next few days look ideal and after that, it's going to be a crapshoot) and you have the permit, this is what I'd do.
Get up to the Portal, observe people unloading and strike up conversations, especially with larger groups. I'd avoid under-25 couples as they tend to be the most anti-social and would prefer to do their own thing (I was probably the exact same at that age). Depending on when you are going up, you'll probably meet people up on-trail as well. It definitely makes it seem to go a lot quicker when you're talking with others. People love talking about themselves, so if you find a group, start asking them questions about themselves and just keep asking questions and listen away, you'll find no quicker path to get a total stranger to warm up to you. You'll learn a lot about people as well such as the key "will this person stick around if I have an issue?". People who show no interest in you (who don't return your question with "how about yourself?" and keep talking about themselves could be a red flag). Sorry for the obvious human psychology banter, I just find it quite fun to try to read the wide range of personalities on hiking trails.
The worst case is you work your way up to Outpost, and if you don't find anyone you want to hike with, just turn around and appreciate that you still had an amazing hike. My wife and I are actually heading up for one more trip this weekend but unfortunately we'll likely be heading downhill around the time you are potentially going up. Best wishes to you and I hope you get to make it up there. I'll probably pass you out there and not even know it!
