Wiring – How to reseal wiring coming through roof after adding an additional coax drop

You've got a lot of different questions, so I'll try to answer the ones I can:

1. Coax sucks because of the necessary bend. You're better off going with a backless box like the one you linked to, because it makes running cables so much easier. (if you have a second person, have them push the cables up from below (or a straightened coat hanger or other wire to act as a needle, if the bundle of cables is too floppy), and then snag it from the hole with a wire bent into a hook) ... which you can't do as easily if you mount a box with little punchouts. Also, you then don't have to worry about crowding the box, etc.

2. It's easier to run lots of cables at once. What what you're planning already, I'd likely run an extra cat5e/cat6 cable, and then get an HDMI-over-twisted-pair (aka HDMI-over-cat5) extender if you wanted to go that route, or re-terminate it for RJ11 if you wanted to change it over to phone.

3. I don't know of any other way to get cables/pipes through the sill other than drilling, and it's allowed for plumbing, electrical, etc, so long as you then spray foam the holes afterwards (at least, it's required in my area, might not be in yours).

4. You only need to line up well enough to get it in the same bay, so you have a ~14.5" target. I cut the hole for the box first, then check to verify the location of the studs (I don't use hardware that requires me to attach to a stud, so I just have to make sure to miss it when cutting my hole), then measure off of some reference point that I'll be able to find down below. (electrical runs, walls, etc.) If nothing else, you can use plumbing or electrical for identifying where the walls are from below.

5. To avoid humidity issues, use spray foam to seal around the cables. (see #3). It may even be required by code in your area.

The best way is to go around the roof, not through it. As soon as you have a hole, you are providing a path for water. You can seal it, but it's always going to be a weak spot. Additionally, if you ever need to redo the roof, it will be a pain to deal with the wires that are now in the way.

Better to come out of wall, then go up to the roof. You still have to seal the hole to keep water out, but you don't have to deal with water pooling/sitting on it. Use outdoor caulk (which is UV resistant) to seal the hole. You can also use expanding foam if it's big or you really want to keep the insulation factor up, but even that should be covered in caulk on the outside (because it's not UV resistant).

If you're using a bare wire, then you should also use a drip loop: this keeps water from running down the wire and driving into the hole.

If you use conduit, be sure to keep it all glued and sealed to keep water out. You can use a cable gland at the end where the cable comes out to keep it sealed.