A few thoughts if I were starting over.
Concentrate first on getting some good maternal cattle. Good mothers, good feet, good udders, enough milk to raise a good calf, easy keepers, no giants and no midgets, consistent looking in type, size, color, etc. Who is most important - your cows or your bull? I vote for the cows. Resist the urge to bring in cattle that satisfy some need for diversity (odd breeds, colors, size, horns, spots, etc). Consistency in the cows leads to consistency in the calves. A consistent set of calves (age, color, type, look, weight, etc) gives more marketing opportunities. I think crossbred cows have more longevity and fertility than purebreds. I think simangus, simmental and angus cows fit well in my area.
Bull and breed of bull - select bulls that fit with the cows to produce those consistent calves. If you run multiple bulls and will market the calves together, the bulls need to be similar in type, color, etc. Changing bull types/breeds every few years will probably decrease consistency in the calves. Charolais bulls have the color/dilution issue. Not as maternal as some other breeds. Also consider the availability of bulls. Here they are plenty of good angus bulls to select from. A good amount of simmental and simangus bulls. Not so many Charolais and other breeds to select from.
Now the real important stuff - take a critical look at the pastures and forage. Cattle convert grass to pounds of beef. Except for some variation in efficiency, increasing growth and weaning weight will require more calories. The cattle need to fit the environment. It generally takes better/more nutrition to produce more pounds of calf/acre. Grass type, fertilizer, stocking rate, forage quality, management practices are all important. Which is the priority - cow quality or pasture quality to produce more pounds of calves? I think both.
This may seem odd but write out your plan. That will make a person think through the issues and remember what the plan is. Changing direction on a plan is sometimes needed, but some people alter their plan too much and too soon. A plan that includes lots of supplemental feed is a bad plan for most people. A plan that results in low BCS is not a good plan either. Management of stocking rate is a factor in the plan.
Work on the balance between cost and quality of things purchased. Paying more does not itself guarantee better quality, but people sometimes have a tendency to go cheap on important purchases. I would tend to start out with higher quality (and probably higher cost) cows and bulls as opposed to lower quality/cost cows and bulls. Even if I started with fewer head. Of course, none of that issue is as simple to implement as it is to say. But the point is that "cheap" stuff can end up being the most expensive purchase. Buying a cheap cow because she will turn a profit vs. buying a better cow that will turn a bigger profit - one is better than the other.
Produce cattle that there is a market for in your area. Not based on just what you like to see in the pasture. A small producer can't do much about the local market except try to produce what it will best pay you for.
I have rambled on enough. Simmental, angus and simangus cows with angus and simmental bulls would be a good starting point and would produce some consistent growthy calves in this area.