I love cabling challenges. Daily
Sorry I missed out earlier this week to help with replies. Been kind occupied at work all week.
The two cameras above the garage carriage lights...easy enough. Drill straight into the garage through the
MORTAR between the outside stone (you can seal this hole up later if needed) at a 5degree upwards angle from the outside. Masonry drill bit will get the job done. 3/8" bit if a single Cat6. Since you will have data cabling in your garage for the 2 cameras, this is a good time to figure out of any other data, speakers, alarm wire....anything low-voltage-wise to put through the garage wall structure (camera out back or on side?). Now you have to decide if you want to home run all these cables back to your network area or put a POE switch in the garage, and then run a single Cat6 feed to your network area.
In regards to your front door area.. you have an wall air gap. I hope you are comfy learning how to patch drywall. You will have to drill from the outside in, then go up through the double header wall frame, travel across the drywall ceiling through the rafters, and hopefully have some pathway to your network area. Again, best to consider additional cabling in this area (alarm panel, inside data wire for possible future iPad near the front door, etc). You have an endoscope to scout out the pathways. You can do the drywall patching yourself (I mean...it's not hard) or can hire folks to come fix it up for you.
Be
VERY WARY of any penetrations up to the 2nd floor from 1st floor, especially garage. You will be breaking fire code in your county (most likely) and any future home inspector will make a note of this for any refi or selling of home. It can be done but must be done properly and by code.
Here is a picture above my 1st floor celing drywall. You can see the joists running left to right. I had to open this up to fix my dry vent. While open, I did extra low voltage cabling
Here are the holes in my ceiling I did for my LED puck lights, surround speakers, camera & data Cat6...any wire I could think of. It's drywall, not poison. Easy to patch. Especially if thinking of repainting