Reroll the game
One day the party came to city and suddently is encircled by many armed guards. They does not look unfriendly, just carefully doing their work. There is imposant man between them, in impressive armor and he address the party:
"Worry not my friends. As you may know, I am the baron and ruler of this land and my dauther is medium. Sadly she is constantly ill. This night she had dream, that may be of great help. She described your party and the moment you will arrive.
She also had vission about very unusual flower, that could easy her illness. There is big forest, just two days west from this city and the flower groes there. Carefully take it away with good a bag ground around its roots, bring it here and I will give you really good reward for it.
You should take the main way from city and about half a day inside the forest the way crosses a stream. Follow it upstream to its origin, it should be like two or three days travel, and it is the place, where the flower grows.
Just be warned, that some people say the forrest is mysterious and there may be a lot of dangers inside. But on other hand there is lot of travelers regularry usign the main way, which did not meet anything strange, so who knows, where the truth lies.
I would send my mans this early morning there and lead them myself, but my daugther said clearly, that nobody from this city is allowed to go near the place of the flower growing, even if she does not know, why it is so much important.
Anyway I already told all merchants in city to keep good prices for you and offer all reasonable help, so you could start your journey as soon as possible. I hope to see you with the flower here as soon as possible. Please take this gold as advance payment for your services."
He hands you some gold and return to his castle with all his guard. Merchants start approching you and offer their goods ...
The party now can do anything they need, there is a lot of contradicting stories about the forrest, the main way should be basically safe (except strange sounds are heard at some nights, sometimes some wolves or other animals attacks, but basically safe for merchant to travel with one or two poorly armed man, single travelers usually also have no problems ... but people are still scared to go too far from the road). The gold you got is good for two week living expenses plus something more, prices are good, people friendly, baron's daughter loved as she helps commoners in need and predicts a lot of problems, so they can be prevented (crop harvested just before big rain, village evacuated before floods etc ..). Promissed reward is nice (maybe daughter envisioned, what would party like to get, be it better armor, special sword or the righ money), not extravagant, but worth a fight or two...
To the forrest
Party is equiped, on the road, the forest is little dark and lot of noises are to hear, but no problems on main road. Following the stream the forrest is darker, sometimes there nearly is something to be seen on edge of vission, etc, etc = not normal, problems to be expected, dark atmosfere (not horror movie, but a step this way for sure). Depending on your style maybe some small fights with larger than usual animals, or not. Natural obstacles are more harder as they go, but nothing to really stop them. Normal villager would be scared to the bones and run away, but heroes are heroes and the reward is good. Finally they are exhousted and need to camp for a night (or at day) to rest ... they set usual guards, they hear strange sounds (natural or not? Who knows?), they feel watched by many eyes - a lot of dicomfort, but no attack ... (## remember this point ##) ... then morning came, they pack for another day and go ...
(## remember this point ##)
Soon they see, that the hills are closing, and there is some light before them, as if cleaning in the forrest. Then from a hide in trees a few Enemies (desribe them) suprisingly attacks the party. After short fight the Enemies are defeated and killed. Around half mile later the is narrow place, no good way aroud and much larger group of different Enemies - clearly the big encounter as usual for this party.
Your problematic character charges up, others follows and fight begin. As expected the character is killed, while party fights as usual and looks like will won after all. Classical.
But then it cames - you say "Please stop for a moment ..." and describe to the problematic player how his dead character open eyes and see the rest of the party aroud. Somebody calls him "wake up, wake up" and they tell him, that he was mumbling from the sleep, then screamed and they had problem to hold him so he would not hurt himself. They ask, what happened, as they was camped and except usual discomfort nothing bad happened (## first remebered point ##) until the characters sleep became unrest. Common expectation tends, that it was some horrible dream only ... (let them play it and give them free hand to work their solution or preparation ... it was just horrible dream, who knows why ...)
Da capo at fine
... then morning came, they pack for another day and go ... (## the second point ##) ... Soon they see, that the hills are closing, and there is some light before them, as if cleaning in the forrest.
Now they may be attacked by the Enemies, or to try set a trap, walk in the forrest and attack from behind ... yes those Enemies are there (describe them, but there are little variations, like different mark on shield, sabres instead swords or something similar small and unimportant) (this is independent group, does not even know about the main group). After Victory/evasion/whatever they continue.
Around half mile later the is narrow place, no good way aroud and much larger group of different Enemies - clearly the big encounter as usual for this party. (and again there may be found small variations, but it is tactically the same - and those Enemies are hard ... they can defeat them, but it would not be easy or short).
Let they manage how they want to the point when the character dies again. Then goes Interrupt and he had just bad dream ... next time there are again some small variation, maybe even some tactical holes covered ...
Let them continue as many as needed (and maybe include some small hints) until the character came with working strategy (or the group talks him to stick to it). Charging up does not work (even if you would need more Enemies), using his class advantages works much better than charging.
This situation can be varied more times if needed, they may run to another group of Enemies more times before they overcome all obstacles. (Cycle only over last encounter.)
The way back disappears like half mile after them, streaam goes underworlds, big rocks blocks the way and cannot be climbed up - tho only way now is forward, not back or to side.
After this confusing part ends (he managed use his class abilities right - maybe more times in row) they reach the origin of the stream, pick up flower and return. (Way back is now normal, dark first, then better, as they approach the road, leftovers after each final battle is there as expected - or maybe even better there are none and just forrest)
In the city they are welcomed, Baron rewards them as promised, invite them for big celebrations with lot of a food, his daugher (medium) thanks them, carefully garned the flower and is visible, that near the flower she looks more healthy and energic.
They may shop as they need and the road calls again to next adventure ...
- The Encounter should be set the way, that (if played correctly) the problematic character would really helped to victory (so lot of place for his special abilities)
- if party tries to just protect the character from dying, near the end of battle he wake up and all repeats ... this is not way to overcame it
- you should warn other players, that you will try something little different and ask them for help and to try have fun even if things came complicated (but do not tell them, what you are for)
- you may alternate the Enemies configuration (numbers, second wave, help etc ...) each time you see hole in your plan
- you should alternate Enemies a little each time - as now it is (hope) real, while the last was just terrible (and not exact) dream
- what are first and second Enemies is up to you to decide, it should be something you group is used to and expecting in fight (be it giants, big Wolves, orc army, whatever) and there may be a lot of usual proprieties, like rock edge to put them over, or old mines to put them inside, ruins of castle ... whatever you are used to make more approaches possible
- princess can tell them afterward, that she had dream about their journey and she had seen them dreaming unrestly in the camp (## point one ##) just few miles from flower under some "strange spell or what" until they managed to woke up for real and bring the flower
- they may discover, that Baron's wife is long time dead and that she may be was some unnatural being (like fairy, undine, mermaid, ....) or not, who knows for sure?
- there may be some shadow just before each waking (god/DEATH/something) who say to the char something like "... and you will not remember it as you woke", next time "... this was also iteresting talk, but you will not remember it as you woke", and so on (and he will not remeber it, as you would not say, what it was about) and finally "... you seem to have lot of fun with it, let me try it too" and this cycle YOU will play the character the way YOU think it should be played and after Victory run interrupt again and let say the shadow "It was really something, I had not such fun in hundred years, but now it is your round" and character woke up on the (##point one##)
- or the shadow would take totally different class and equipement (and YOU tell other players, that for just this cycle their chars remeber the affected char as this class (say Beserker or what) and play it in the "charge up, tank all" way with proper attributes and equip to the Victory (and it should be reachable with such character without cheating), then the shadow will return the "normal character" - and you may offer to the player to change the build to more fitting, and make agreement, that it "was already this way, as far as chars can remember"
- the Encounter should be hard, but also short enought to fit in one session, or (if possible) fit there more times, to not waste too much time repeating it
- players can "train" this Encounter and use knowledge from last iterations, Enemies should not remember last iterations and fall to all traps, they did fall before (until it is hole which would undermine the story)
- each cycle starts on the same point, so no loot or EXP are get and nothing is lost/used (arrows, bombs ...) - just like "savegame" on computers, but if there was lot of cycles, I would increase the reward (to cover some "lost loot") and gave lot EXP for solving it and delivering the flower (again to cover some of "lost EXP") - even if it was dream, players spend time and characters get some insight and experience by working hard in the dream