I'm in the camp that foresee irregular streams in the distant future, just whenever he actually wants to stream something, once he's comfortable again. I doubt Vin would retire from streaming entirely, he owes a lot to it. Vinesauce is what helped him out of a dead-end, painstaking job, helped him move into a better house, meet several long-term friends and propagate his music. Plus, he does genuinely enjoy playing video games & offering commentary, shallow as it may be.
I wager he'll be back in time for the charity stream because he seems to believe in the cause, besides, chat was somewhat more moderated due to the PCRF connection. However, he probably won't stream for Vinesauce's anniversary. We can expect pre-recorded videos then.
I only hope that, for the love of God, people stop drawing creepy art of Vinny on the buroo. He hates it, most of his sane viewers find it uncomfortable and it's just all around fucking weird.