Some probably know some of these things, but for those who don't, it should shed some light on how the timers work.
The VIP timer is 4 real life hours. After that time expires (or you retire) you must wait 12 real life hours before VIP will be able to be activated again.
However, there are ways to sort of "circumvent" the 4 hour rule. The VIP clock stops whenever you do something outside of freeroam. So, if you are a VIP and you:
Sign out of GTA Online, the clock will stop and you'll be able to pick up where you left off when you log back in.
Join a mission, heist, race, etc, the clock will stop and you'll be able to pick up where you left off once re-entering freeroam.
The timers to do the "VIP Work" are on a nonstop timer, like the 12 hour wait to become a VIP again. I'm referring to a timer that doesn't stop regardless of your actions as a "nonstop timer."
So, taking that into account, the options available to do as "VIP Work" are:
So, say you do "sightseer." Once the event ends, you have to wait 5 minutes real time to activate any of the other 5, or wait 10 minutes real time to activate "sightseer" again. But, again, there is a bit of a way around this:
Say after finishing "sightseer," you have 2 hours of VIP time left. Joining a mission (or heist, race, whatever) will stop your VIP clock, but the timers to redo the "VIP work" will keep rolling. So, if you do a race that lasts 5 minutes real time, upon respawning into freeroam, you would be able to run any of the other 5 "VIP Work" (the exception being sightseer).
Other things I've noticed:
1: If you have 2 characters, if one has run out of VIP time (by killing the 4 hour clock or retiring) you can still be a VIP on the other character.
2: The following "VIP Work" can be done in solo in an invite only session. Obviously, you have to be the VIP: Hostile Takeover, Asset Recovery, Sightseer
From my experience, sightseer pays the best and is the easiest. Just grab the three cases and get paid. I've made over $20K each time doing this. The others paid less and involved more work (evading cops or killing NPC's... Nothing major, but more than simply collecting cases) but, I only did Hostile Takeover and Asset Recovery once each, so pay may be different, pending on how long it takes to finish, etc.
Just some things I noticed and hopefully answers some questions for some that were wondering.
OK, very small addendum to this...
There is a time, albeit relatively brief that, after doing something out of the "VIP work" list, the game doesn't realize that the event is over, which would start the the cooldown timers to do them again. If you leave freeroam BEFORE THE GAME STARTS THOSE TIMERS they won't start until AFTER YOU RETURN TO FREEROAM
Just to be safe, after I finished running "sightseer," I went in and MADE SURE that the "VIP work" timers were running. Once 5 seconds or so ran off, I knew I was good. Once the timers start, you should be fine. Personally, I immediately bank after events and this seems to be enough time to get the cooldown timers rolling. However, I go back in the menu just to make sure.
TL/DR version: Wait until the "VIP work" timers start rolling, after completing something out of the "VIP work" list. Once they start, you are free to go do your mission, heist, whatever and the cooldown will continue to run.
Hope this makes sense.
Additional info: Added 10:35PM EST
Just some additional things I found out during my time as VIP that I thought people would be interested in:
If you are in any "VIP Work" when your time expires, you remain a VIP until it is complete (in other words, you don't get cut off in the middle just for running out of VIP time).
"Cooldown" time on vehicles seems to be 2 mins for VIP's.
While a VIP, you unlock the VIP tints for the Revolver and Switchblade (Duh). But, if you don't buy them during your VIP time, they will re-lock until you become a VIP again. After buying the tints, you can use them even when you're not a VIP (I assume the same is true for the bodyguard tints).
Pay is indeed dictated based on how long the "VIP Work" lasts. I only tried this on the aforementioned "Sightseer," but am relatively sure that this will be the case along all of the other "VIP Work." Sightseeer is on a 15 minute time limit. For those interested, payouts I recorded are as follows:
Finish with 10:30 remaining: $22K payout
Finish with 9:25 remaining: $23K payout
Finish with 5:00 remaining: $24.5K payout
Finish with 4:59 or less remaining: $25K payout
So, if you're grinding, common logic might suggest that you finish it with 4:59 remaining every time. But, at least IMO, I would suggest aiming to finish them as soon as possible. Look at it this way, as an example:
Finishing it with 10:30 left, you make $3K less than if you finish it with 4:59 left BUT you also save 5:31 on your VIP time AND get the cooldown timer moving 5:31 quicker. In this instance, where VIP time is limited, the extra 5:31 is more valuable than the $3K, again, at least IMO.
Of course, you might not finish it with that much time EVERY TIME but any way you slice it, stopping the VIP timer and getting the cooldown timer running as quick as possible is better than sitting around for an extra $3K or less.
Of course, if you start "Sightseer" without enough time to allow the cooldown to finish before your VIP time is up, obviously maxing the payout in that scenario is best.