I am trying to solve what is supposed to be a simple word problem in a riddle book, however I cannot seem to come up with enough info to set up a system of equations. Am I going about this the wrong way?
All it says before this is "There were two Sers, Ser Manfryd and Ser Raynard, the two families had more in common than they thought."

I set up the equations: with vars as:
d = dad
m = mom
s = son
(s-1) = daughter
I got
d + m + s + (s-1) = 100
(d^2)= (m^2) + (s^2) + (s-1)^2
After that I have no clue where to go. Any hints?
Suggestions:
From your first equation, $d+m=101-2s$. From your second equation, $d^2-m^2=2s^2-2s+1$.
Therefore $2s^2-2s+1=d^2-m^2=(d+m)(d-m)=(101-2s)(d-m)$.
So $d-m=\frac{2s^2-2s+1}{101-2s}$.
Try values of $s$ unitl you get an integer for $d-m$ (remembering that $s$ is the son's age should help figuring out reasonable values to try).
After a while you get (integer) values for $s$ and $d-m$, from which you should be able to find all the ages.
The other family can be dealt with similarly.