Hell, I do not read for a couple of days and then tons of messages appear :D
Anyway, I like you consider what we say, so I leave some comments
Contamination is working now too. I'm not sure about random illness, I think it's realistic but the player might be too pissed. It's kinda unfair gameplay-wise. Right now illness only happens if you overwork your painters. Let me know if you lurkers have any opinions on this.
I think illness should happen. You can cure the man with rest (common illness) for a certain period of time.
For sever illness you can hire a medic, it takes more time.
Really rarely, he can die for some illness, maybe in contemporary with a pandemic (eg: black death).
Indeed it is frustrating for the player, and for this reason there should be a compensation of some sort (money or skill gain for the new oldest\better painter in the guild)
Or, you can put an option to remove illness, so there will be more challenge for who wants it, and a smoother gameplay for who wants it easier.
You can try to prevent death.
I'm not sure if this specific event will be going to the countryside. Now that I think about it, I think the solution here would be to hire a doctor. Resting should be a solution for when illness has just begun, not for this stage.
Will have to read about medicine in the Renaissance.
Well maybe you can try both: first hire a doctor to try to cure your painter.
If he's going to die for sure, you can send him to rest and enjoy what is remaining of his life in the countryside.
You could also add the event of the old painter who want to retire and live the last years of life relaxing :D (maybe this is already present in the game, I don't know)
Edit: an idea to incorporate famous painters (Leonardo da Vinci, Michelangelo etc):
"A great artist is looking for a guild. He/she will join you if you can fulfill the following:
-Have 2000 Florins
-Guild has 5 rooms
-2 Artists of the Sfumato style
-1 empty painter slot
Time (years?) remaining: X"
nice idea.
Or you can be so lucky to discover them from youth?