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Partial Reply:

SERVANTS  thing   (cause I  *KNOW*  wasn't in 5.3!)  
*REALLY* wish he'd put that in the CHANGELOG!   (with all this other  [mostly making it HARDER!]  stuff--that's  (only?)  thing making it easier. )

Think I wrote that  (Succubus)  b4 I looked @  all you saves...   Post  D20, right?     [Probably the most useful thing about hookers,  but it takes a *LOT to get them!  --->  PLUS,  looks like you never used your hookers on your combat team, right?  (only for GOLD?)  --  Also means they R *NEVER* @  Risk for the  "death"  hi dam/ etc  penalty  (so good insurance keep gold/production high!) ]  

I too often get unlucky in  (well pretty much everything lol)  shop rolls.     BTW  (sucks dev!)  Heavy armor   costs a *LOT* to BUY,  but SELLS  for almost NOTHING!  :-( 

"....and no I never bought a staff."  ----WOW.    [1  BIG difference right there!]       (need to check on that   "higher wits  =  better healing  [W/O STAFF]  claim.  ) Unless he changed that,  I  *KNOW*  MATK  depends upon  STAFF Bonus  & "Lessor Heal  is  120%  of MATK"    (Looks like you had  3 mages,  & *ONE*  staff,  so...  )     Maybe that's another recent change??? 
(VERIFIED:      Even  W/O  staff,  hi wit   (tested Daisy vs Greph ----your save)    heals more!    [32   vs 21!]

ok,  in my own defense don't know what version tested this in   [VERY new to 5.4]   but this did NOT used to be the case!   Used to be,   heals only depended upon MATK   (which is very strongly influenced by staffs)    Nothing about that in the Changelog Either

Sidenote:   Your  "combat team"   I did notice you don't  "mix & match"     (ok,  Daisy)  ----ie,  except Daisy,  NONE  of your team was Workers/Fishers/Hunter/Farmer.     Every class was military or could B used in fights.      [BTW   1 Grave  Injury  = D13]

-->>    What's   the  *EARLIEST*  day you did combat?       (matters a LOT in 5.4  with the  Enhanced  "super powered"   Enemies!)
(D9 you had 3 hookers but only  3 combat char-----wait Wiki  [hooker]   had club,   so  4 combat?       [a lot of my combat----including that  "EASY"  quest w the  "60 Evasion  [UGH!]  Rebel-----were QUESTS,   so did them early.   (b4  D14?   maybe  b4  D7?)

-more than one thief-----Evasion bonus?

=====================================

Thinking of Trying a Run ---Fishers   (instead of your hookers)----but honestly could also be done w Worker   (wood/iron), Hunter  (meat)  or Farmer  (cloth)     **CONSOLIDATE**     (like you did---maybe more?)  I don't usually  do this either.     Usually char get BOTH "Peace" & "war" classes --->>>   BUT EVEN *ONE*   "Grave Injury"   is more than enough to kill this   (CRUCIAL---esp  1st 14 days!)  Production!

I take time to write too  (mostly if long ones)  sometimes ck notes /saves /etc)

Not sure about Upgrades.   [5.4]  
BIGGEST  *HUGE*  problem so far  [5.4]    has been *FIGHTS*;      Even EASY  Quests can have them,     [new  "super-powered"  enemies!]