I used to have an extremely hard time getting my dough to stretch out without tearing. It was when I was using the original New York recipe posted on this site (it's also posted on another site, not sure where the recipe originated, but anyway). I think it was because of the long kneading time (full 15 minutes). I could be wrong about that though because I have totally abandoned that recipe and now almost exclusively use the Lehmann formula using percentages.
I have two digital scales now. One for the flour and water and another one that I use to weigh the salt, yeast and oil. It is
much easier than trying to measure everything and as I'm sure you know a
lot more accurate.
I have never used a rolling pin for pizza. As far as everything I have read or seen on TV and whatnot it's a major no-no. The funny thing about this is that the best pizza place in the town I live in uses one. You never get any bubbles or anything because of it but they still have the best tasting pizza in town. They use a deck oven and they also use escalon products for their sauce.
I too had a problem getting the peel figured out but I have it figured out now. The biggest thing I have noticed is using enough flour (or whatever it is that you like to use, personally I like semolina flour) on it to keeping the dough from sticking (without using too much). That and assembling the sauce, cheese and other toppings as quickly as possible to keep the dough from wanting to stick.
As far as your dough not stretching out easily I have the opposite problem now. It stretches almost too easily. I really can't "hand toss" it because it would be too big. I am going to experiment with using less dough soon to see what happens though. Right now I am using about 19.6 ounces of dough for about an 18" pizza.
If your pizza is better than the local joints then you are on the right track for sure.

Oh by the way, I use about 7 ounces of sauce for the my pizzas. I'm not sure what everyone else on here uses but for the size I am making it seems to be about right. Not too much but enough.