How often do you re-silicone and how long does it usually take you? I usually do it maybe once every three months and it usually takes me half an hour to an hour because I tend to be a perfectionist.
I do it about once every 1.5-2 weeks. It take about 5 minutes to apply it and 3-4 hours to set, I don’t use flowable, I use Red RTV.
I do it pretty much at the same time interval. It’s really whenever you feel like the yo-yo isn’t responding as it should (your binds tend to slip, string is loosely wound after a bind, etc.).
If I’m working with flowable silicone, I tend to be a 5-minutes-or-less kind of guy, whereas RTV takes me somewhere on the order of 10 minutes, excluding the time it takes to clean out the old silicone.
I don’t.
Ever.
Too lazy.
Well that explains the Punchline being returned to me with only one side still siliconed… 
It takes me about 20 minutes with Red RTV and I do it whenever I bind and it doesn’t come back up, so like every 3-4 months.
YOU DONT EVEN KNOW WHAT IVE BEEN THROUGH WITH THIS KID
Never unless it falls out or tears.
I don’t silicone my yoyo(s) unless my binds get slippy, or the “ring” gets torn or worn out (Which is the main reason why I like the DM better than the DM2). It’s sort of a drag to have to keep buying silicone (whether it is flowable or rings from YYJ or YYF etc). With a hybrid yoyo, you don’t have to do anything to it. You can just keep playing with it forever with tight binds. But aside from that, your second question, I wait a full 24 hours for my silicone to fully dry. If you don’t think you have that kind of patience, either wait AT LEAST 6 hours, or buy more yoyos. Hope this helped. 
I told you! I would get you back.
I’m just bustin’. Q’s legit. Don’t worry yoyojamben, you’ll get yours.
Me and him have dealt before Julian.
I wrapped a string around the yoyo, but didnt attach it. He was being a little doofus, so I told him I’d get him back. That was how. lol
Same here, but it really only takes 5 mins tops per half. then at least 6 hours to cure/dry. but yeh, red RTV is much more durable than clear aquarium silicone.
Werrrrrrrrd hahaha. Well then in that case yoyojamben, you got yours! 
^
I once got a knot in a friend’s P2 and just put it back in the case because I didn’t feel like digging it out…luckily he had ninja skills.
I re silicone whenever 5a length string doesn’t bind tight because my 5a string is much shorter than 1a.