Hi Rhand,
I understand your frustration - R:TW was designed to be almost impossible to undergo a complete conquest with - especially with a Celtic (Gauls, Britain and Iberians) Barbarian faction - the Germans are slightly easier to win with due to their better unit roster.
Automatic resolution is heavily imbalanced - some units are drastically over-powered in auto-resolve compared to their battlefield ability, and others are drastically underpowered. It is often better to play the battle out since you then have the ability to use tactical flare in organising your victories - the AI simply isn't as intelligent as you in R:TW.
To prevent squalor, the best option is to simply prevent growth - as a wise fellow once said - "your war is not against squalor - it's against population growth". Population growth will always occur in even the least hygienic and well fed settlements, yet it can be slowed down by avoiding health and population boosting buildings, including farms. Sadly, though, since to get the best military units you require maxed up cities, so, in certain strategically important cities, this rule will have to be broken.
Unfortunately, your only resort against squalor, once you have it, is building heath buildings and similar happiness structures, as you have said. I do believe, however, that they do not actually resolve squalor and instead simply counter-act and, over time phase their good out by piling huge amounts of population upon your settlement creating a worse squalor issue. You could also upgrade the Governor's palace, yet that can make things worse in the long run too.
The best thing I find if the problem is too out of hand is abandoning the settlement, leaving it to revolt, and then returning to exterminate the populace. It reduces the population's numbers, yet also removes income within the settlement, so, if your desperate for cash, then you may wish to avoid this evil strategy.
May I also suggest that you try rebalancing the population. Simply train many units of peasants in your largest cities and disband them in your smaller ones. This migration moves men from the large city, that could do with less people in the populace, to a smaller one that requires the population to expand to the next level to gain better troops. If you have no small cities that require this boost, send the Peasants to their deaths - stick 'em on a boat and send them into pirate/enemy infested waters (or in your case Brutii lands). They will soon be dead, leaving you with nothing to worry about!
On the monetary side of things, as the Barbarians, poverty is almost guaranteed! They are pretty hard to manage compared to other factions (I congratulate you on making it this far - I'm too lazy too!). If you haven't constructed Markets and Ports and upped the tax rate, then this may be the time to do so. However, do try to avoid sending your populace down to red, although you can afford making them blue. It also may be a good idea to wipe your existing temples and build law boosting ones, if the Britains have them - they reduce corruption in your settlements providing you with a much higher income! Moving the capital to a centralised position does the same too for reducing corruption. Finally it may also be a good idea to kill those stinking rebels sitting on your roads and those pirates blockading your ports - they both destroy your trade further reducing your income!
Good luck with your map conquest, cheers!
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