I wish more of the spaces I’ve worked in looked like that.

Nice to have a reference point (where the light leaks in) to get oriented right away and no insulation or junk in the way of where you expect stuff to go.
Mounting the box for the transition in the attic where it won’t be seen is ideal, yes. That way it’s still accessible as required, it keeps your NM indoors, and is not an eyesore.
If I’m going to be working in an attic space with no decking for any length of time, I tend to toss in a few strips of plywood, sized just small enough to fit through the attic opening. It makes things safer and a little more comfortable. Sounds like you’ve more or less already done that to make your catwalk. You can decide if you want to secure something up there for future use (you know, for next time you’re up there to install ”just one more camera”), or just do something temporary to make life easy while you install the box and conduit.
Inside the attic, you can locate the box where it’s convenient to work in/on - there’s nothing that says it needs to go right out near the eaves for the transition. If you place it away from the eaves, more towards the center where you’ve already ventured, you’ll have more headroom (watch those roofing nails) while making your connections and such. Of course, the further from the eaves you go, the more conduit and wire you’ll need but the cost won’t change much for such small distances.
You should be able to drill a small pilot hole from outside, right where the conduit will naturally want to sit when attached to the exterior surface mount box (like the picture you shared previously). Then use that small hole to feed a fish stick or coat hanger up and check precisely where it’s going to wind up in the interior space. You can wrap some brightly colored tape on whatever you use to make it easier to spot in the attic. Hopefully it winds up exactly where you expect it but if not, it’s best to find out with a small hole that’ll blend in with the ventilated soffit.
If it looks good on the inside (i.e., you’re not going to drill out part of a joist or rafter tail with your larger bit sized to fit your conduit or some other show-stopping-problem), then you can drill the hole to the final size you need. After that, it’s just a matter of feeding the conduit in through the hole from outside (to avoid having to work laying down in the narrow space in the attic where the roof meets the wall). It should be fairly easy to guide it where you want it to go with flex.