I understand that my chances are better at winning the lottery are better than guessing a block, but humor me please. If I have a pool with 2 miners will my miners offer more "guesses" at the block hash with a difficulty of 512 than they would with a difficulty of 1024?
The difficulty roughly means your miners finding a single nonce that results in a block hash that starts with a certain number of zeros.
The Bitcoin network requires a very high difficulty. Of course, it is unlikely any of your miners will actually generate the hash that the Bitcoin network wants. So, instead, you sign up to a mining pool. However, the mining pool needs to gauge how much work your miner is doing. So it asks your miner to try and generate hashes but with a low difficulty threshold. Your miners report these hashes instead, which are easy enough that it will successfully generate them. The pool counts the number of these easier hashes that your miner submits to calculate how much work your miner did, and calculate your fair share of the block.
Lowering the difficulty doesn't change your hash rate. It just changes how often your miner reports proof of it doing work to the pool.
Just by random chance, one of these easy blocks of work will have enough zeros to fulfill the Bitcoin network's difficulty requirement. The pool will submit that one to the network to claim the block reward to distribute to the members of the pool.