Now at the home run, how am I going to get it past the foundation into the garage ? Is there enough space somewhere that I can take the wires out to the garage from the crawl space! Do I have to go "up" and then across into the garage?
Over the years here have added more LV to the garage. I did also add more HV the garage. The attached garage had two sections of two walls that were common with the house. Initially the endeavor started by adding LV then later water. (put a sink in the garage). Some was already roughed in. I used the same or similar paths (not adjacent though) to get under the home into the basement for my adds. Also found a path for a gas line as the laundry room and gas line was close (well sort of). I also used the attic space of the garage as it is another attic that is not part of the main house attic for adding electric. It was a PITA to get to that attic but I could and did run new conduit in it (which ends up in the basement).
I am leaning towards continue drilling from bottom and see where I come out.
Go slow as it will be very low on the WAF if you hit that carpeting with the drill bit from the bottom. Put a bright light in the space either above or below; might help a bit. The smaller the opening for drilling the more difficult it will be to drill straight up or down. Thinking my drill has a level bubbles on it.
Except in special cases—when you intentionally choose a specific angle or bias—it’s important to keep all drill holes perpendicular to the surface. This is easy to accomplish with a drill press, but there are plenty of occasions when you need to use a hand drill/driver to complete the task, like drilling into a wall or cabinet door. Many drills have a bubble level, but those can only help in certain situations, and most walls are not exactly flat or straight.
One option is to buy a specific type of jig—a portable drill guide. You can also whip one up at home with some wood scraps for an easy, no-cost alternative.