Assuming we are following what I hope is conventional wisdom, the timing corrections for joins to the hold are the same as those for outbound leg in the hold i.e. +/- one second for each knot of headwind/tailwind. The question being asked here is when to start the timer.
Regarding sector 2/offset joins, you won't be turning for much more than 10 seconds to intercept the QDR which defines the join. It could therefore be argued that you could add 10s to your calculated outbound time to give yourself a bit more room prior to making the inbound turn after the entry. This will of course tend to put you slightly wide at the end of the join and you are likely to intercept the inbound track from inside the hold. From a test point of view it could be argued that if you fly for the pre-planned amount of time you will have less opportunity to make a cock-up of tracking the QDR, although the flip side is that you will be closer to the beacon when making the inbound turn.
With sector 1/parallel joins, consider the following. if you are joining a right-hand hold with an inbound track of 090 (draw the picture) and the wind is 090/30, you would expect to fly outbound in the join for 30s. If we were joining the hold on a heading of 360 (remember hold entry is based on heading, not QDM as most of my students seem to think!), we would take 30s to turn from 360 onto our join heading of 270. If we were to turn inbound 30s after crossing the beacon, the chances are we would be rather close to the beacon and it would be quite difficult to intercept the inbound track. And yes I know you are allowed to track straight back to the beacon but it does make life easier if you intercept the inbound track in a parallel join so that you are more likely to be in the right place when turning outbound in the subsequent hold. Bearing that in mind, and assuming you've got this far without losing the will to live, it makes sense to restart the timer when wings level on your outbound heading in a parallel join. I think!!!
Looking at your nice diagram of the above scenario, and changing the wind to 140/30 to push us further outside the hold in the join, note that there is every chance that you will end up intercepting the inbound track from the non-holding side, or even turning onto the inbound track as if by magic. That one usually really confuses the troops, even when they've been pre-briefed.
I've been instructing for 8 years and am currently at a southern-based flight school which is suddenly quite a popular topic on pprune. This is the first posting I've made so I hope it at least makes some sense!