Calj
Are we thinking he either has a wasted wiper ring , a valve guide seal issue or both in #3? His compression numbers didn't look that bad (with oil) a couple of pages back. Of course there is no easy way to inspect either of these items and if he will break the engine down to change one issue he might better do the other for sure. And as you say the chains ,while he's got it open and the top end weight is off, might better take er out of the cradle and do a complete chain replace and check those bearings out along the way.
Riv
You'll be up to armpits with the top end anyways, and it's not as big a deal as you may think it is to split the cases especially once you've taken the top end down. I find that the biggest time consuming pita is the valves, cleaning , lapping cleaning some more ,then cleaning it again..... I magnetize a screwdriver to set the keepers cause I have sausage fingers ( which has also interfered with the idea of playing a guitar), but that is really the hardest part and most time consuming for me. I need 4 hours of uninterrupted time just for that. The rest is easy, if you let it be. So don't panic, it's all good. Fun and worthwhile.