Well - let me first make a few things clear to help out, then.
1. You only make 1 roll per month - your Income Roll.
Of the income roll - you should note a few things that seemed to confuse people.
A. Your building bonuses are 1 month behind. For the first month - the only bonuses you get to your Income come from your Council Members only.
On month 2 the buildings you started work on for month 1 are finished. So on month 2 all the bonuses you gain for buildings are there.
The buildings you work on month 2 have bonuses - but they don't show up until month 3 - and so on.
In short: all bonuses from buildings happen one month behind. You don't get the bonuses until the month "After" you began working on the building. Then - after that - the bonuses kick in. Please talk to me if this is confusing, and I will try to explain it better.
B. You are the "leader" of your barony; and you have a "Deputy Mayor". These are 2 different people; and though the book says you can have "two leaders" - this does not apply to your barony for the first year. It's either your Charisma bonus, or your Deputies Charisma bonus - despite what the book may indicate - for the first year - you only have ONE Leader to offer an Income Bonus via Charisma.
C. You should set a tax rate. Once you set the rate - you are better prepared to achieve success. A 5% tax rate can lower your Baronies income in taxes - but it also lowers you Income DC to 30.
Regarding weekly checks
You are absolutely incorrect. It is so easy that it hurts. In fact - because it is so easy - absolutely none of my players can seem to get the concept - so I don't blame you.
Let me state it another way:
Each week you can take a "Natural 20" in one skill of your choice to do something very important for your barony - you decide whatever it is. Maybe you want to set up a embassy - or scout your borders for bandits - or try to solve mysteries with knowledge checks.
Whatever it is you want to do - you can make that check - with a natural 20.
The question is: will even a natural 20 be high enough to be successful?
For example - if Arasmes wishes to see if he can have a man swim to the other side of a river (though I don't know why) - he could take the natural 20 for a "Swim Check" - and probably fail anyway.
Or - he could say "I order my barbarian Corsair to swim the river!" - and if THAT guy did it - he'd have like a 35, and succeed with ease.
SO - all you have to do for each week is pick one thing you want to do. Just one thing per week - then, all you have to do next is take the natural 20. Will it be an auto-success? It all depends on which Council Member you elect to do the job - and what their bonus to the skill is.
Okay - I hope that helps.
Please let me know if there is any other follow up questions.