MacSideJosh >> How hard can I push around the epoxy to saturate the cloth?
Depends on what you push with. Basically, you want to push hard enough that excess puddles are moved to dry cloth but not hard enough to damage the glass fibers. If you push too hard you "overwork" the glass. That is, you pull tiny, almost invisible, fibers out of the threads. They accumulate in the epoxy and form the dreaded glass snot which is very messy and distracting to deal with.
Pushing too hard also moves the glass around and can leave you with unexpexted bare wood and/or bubbles. Not pushing hard enough leaves you with excess epoxy and floating glass.
A squeegee is a good tool for moving the epoxy. It naturally moves the excess away from puddles. However, because it concentrates the pressure along a thin edge it can easily overwork the cloth. If that edge digs in, it can damage the glass, too. The only way to get good with a squeegee is through practice, but once you do get proficient with it it does a very good job.
My personal favorite is gloved hands. There's no sharp edges and I can actually feel if the glass is too dry or if there are puddles and the glass is floating. I can also feel how much pressure I'm applying and correct instantly. The downside is that it's messy, especially if I have to change gloves.
Remember also that if things aren't going well you can always peel up the saturated cloth, move it around and smooth it down again. If it's really bad you can peel it up while it's still wet, throw it away and try again. You don't have to settle for bad glass on your boat.
Finally, a roll of paper towels is your friend. Once the glass is down and still wet, roll paper towels onto it. Let them sit for a few minutes to blot the excess, pull them off and tip the bubbles with a foam brush.

Blotting saturated glass leaves you with pretty much the perfect glass/resin ratio for maximum strength and minimum weight. The weave is completely unfilled and visible but the glass is completely saturated. Once you have the glass like this, you can keep applying very thin coats of epoxy just until the weave is filled to get minimum weight.
Have fun,
Laszlo