Let's talk about everyone's favourite Lord and Savior.
Everyone knows why this card is good. I don't need to talk about agenda flood or countering indexing or recycling economy cards. It's easy to use this card to get out of a losing situation, but nobody really talks about how to play him to get an edge and win.
When I was just starting to be of intermediate skill, I would treat any agenda in HQ as a liability, and get rid of it with jackson as soon as possible no matter the circumstance. After all, the corp is "on defense", you can't let agendas get stolen, right? But if you treat your agendas like a liability, that's all they will ever amount to.
In Magic, in Legacy in particular, they say to newcomers that the best way to play Brainstorm (that's the card I butchered, above) is not to play it, i.e., to wait many turns until you have 2 totally useless cards in hand to shuffle away, making the brainstorm effectively "draw 3", not "draw 3 then put 2 back". Likewise in netrunner, if your hand is already good, even just average, it's often a waste of time to overdraw. "Mulliganing" with jackson isn't free -- it takes 3 clicks that you don't get to spend advancing your economy or board, and (especially if you're playing a long-game deck like RP) you're committing jackson to shuffle back agendas instead of econ, making R&D more likely to betray you 10 turns down the road.
With a few rare exceptions, to overdraw with jackson is to durdle. But there's always a point in the game where the corp has advantage for just a scant few turns, after which the runner will overwhelm them. A corp who durdles past that point dooms themself to lose on R&D much later (and perhaps not even realize why).
Okay, enough abstract babbling. I don't have a definitive guidebook of all the sweet plays you can make with jackson, but I have a few examples to share.
First, recently I was spectating a game where the corp made it safely into the late-midgame (20 or so left in R&D), but had a fistful of ice, no money, no agendas scored, and was having trouble fending off siphons. Rather than click for credits, they took a mulligan with jackson looking for hedge funds. This is wrong whether or not money cards show up -- without any agenda points scored, they need the game to go long, but if it does go long, having overdrawn would just cripple R&D's ability to protect itself. Install jackson, click for cred twice, and shuffle back the hedge funds already in archives would be much better.
Second example. I was playing @servas in the league, my Andy vs his RP. I've killed all the econ assets and connected with several siphons and scored one nisei, but through it all, the giraffes helped rez most ice and score a nisei token. R&D is down to 10 or so cards, but nevertheless, he overdraws with jackson. I know he's a good player, so he knows he can't durdle here, so I know he must be digging for the second nisei rather than mulliganing. I can't let him IA it. Rule of thumb is that after jackson-draw-2-draw-2, legwork will whiff, but here I was able to use legwork to force the nisei token on HQ, leaving him unable to safely score and letting me slowly win on R&D.
Example 3 - Playing @Paranoid earlier today, my ETF glacier vs his Andy. We were both on 5 points and both poor, so I was trying to bait him into my remote with face-down assets (bluffing as 3/2s). By the time a 3/2 finally showed up, R&D was down to 12 cards, I had put jackson in the remote and discarded a 5/3 (for 2 agendas left in the deck). On autopilot, I shuffle back 2 operations and the 5/3, hoping to close out the game with my 3/2 before he wins with RDI. He won next run. What I should have done was leave the 5/3 in archives for 50% better odds not to lose on R&D, since it's not like a crim with sec testing will ever actually check there right after a jackson shuffle, especially not with as much pressure as I was putting with a fresh card in the remote every turn.
There's my story. You got any experiences with learning how to play jackson more skillfully? Using him for aggression rather than defense, watching what he does as runner to read the corp's mind, or bluffing with your shuffles to give the runner the wrong read? Please share!