Is Wiring Your Home Worth It?
Then, it was time to cut and drill. The old-construction mud rings I purchased included a handy guide, to ensure that I cut the proper size and shape hole in the wall. Then, it was just a matter of getting my bendy drill bit started, applying the appropriate pressure, and drilling through the floor into the crawlspace, and praying I didn't hit a gasline down there. Luckily in the 50s, when they built my house, no one put insulation in the walls, so I didn't have to deal with that while drilling my holes.

When you make turns with data cables, it's important not to use too harsh an angle, or you can actually impact your data transmission speeds.
After the holes were drilled, it was time to head to the crawlspace and start pulling cable bundles. I pulled them to the drops, which I was able to find by turning out my light in the crawlspace, and having someone shine a light down the hole. Because there's no insulation in the walls, I was able to easily push the cables up through the hole, and have someone grab them and pull up a few feet of slack--you don't want to accidently not pull enough cable. Then I used some cable tacks to fix the entire run to the central support beam for the house. I did that for each room that I needed phone, cable, or Ethernet, and moved on to the central wiring step.

Make sure you don't actualy crimp the Ethernet cables when you're tying the cables down.
From there, it was as simple as mounting Ethernet jacks on each end of the run using the instructions provided with the jacks, mounting them in faceplates, and screwing the faceplates on to the wall. I ended up using a D-Link multi-voltage Power over Ethernet device and a compatible D-Link switch to push power into my crawlspace give me an easy way to get data flowing to each port.
After living with the results, I can happily say that the work was definitely worth the effort. I'm seeing stupid-fast file transfers across my home network, and it's really nice not to rely on wonky Wi-Fi bridges or expensive Powerline adapters to stream video and make VOIP calls.