Because you don't know the height at the bottom of the hill, it would be wise to set h=0 at the bottom at the hill, so you would get mgh=0, exactly what you have. I'm not really sure where your confusion is coming from, so I'm just going to take a wild stab here and tell you that the 2 v's are not the same. Meaning the energy conservation equation would look like this:
1/2m(v1)^2 + mgh = 1/2m(v2)^2
where v1 is the 14.1 and the v2 is the speed at the bottom of the hill. On the LHS h is 10 and on the RHS there is no mgh since we let h=0 at that point. Notice the mass just cancels out nicely.
Edit: After thinking about your question again I think I might see the source of your confusion. Potential energy comes from height. So at the bottom of the hill mgh=0, while at the top of the hill mgh=(100)(9.8)(10). I don't really see your logic of setting mgh=0 to 1/2mv^2, mgh(at the bottom of the hill)=/=1/2mv^2 at the bottom of the hill. But rather it's the sum of mgh and 1/2mv^2 at the bottom of the hill= the sum of mgh and 1/2mv^2 at the top the hill. But then you seemed to corrected your own contradiction with the correct equation for energy conservation. So I'm just thinking you're confusing the two different v's.
But try to think about it in a different light, you're using the conservation of energy here. So is the speed at the bottom of the hill really relevant to the question? Is finding the speed at the bottom of the hill necessary to solve the problem? What you are looking at here is conservation of energy. We know that the sum of all energy (including potential) at the top of the hill is the same at the bottom of the hill (where it is all kinetic). Pretty obvious from the earlier equation:
1/2m(v1)^2 + mgh = 1/2m(v2)^2
Now, let's look at the equation you have earlier for S:
S (Hypothenuse) = (1/2mv^2- Mk*mg*cos(theta)) / (mg*sin(theta))
From the construction of your equation, you're saying the initial energy is only kinetic, therefore the v here should have been v2. That's the fundamental mistake in your first attempt, you assumed the v here is v1, but if you used v1, you're not including the gravitational potential energy that should have been there. To take this one step further, you also have:
1/2m(v1)^2 + mgh = 1/2m(v2)^2
Where h here is the first hill, so 10, m=100kg, and v1 is readily available from your answer to part a. Do you see a nice substitution here that can bypass the need to find v2?
A lot of things here, sorry if I sound confusing >_>