Id argue 90% of home ownership boils down to trying to keep outside air and water out of the house. If you can do both of those, you're winning the battle.

That's signs of a water leak. The flashing around your vent is either non-existent, or is failing.

Yep. Any time they throw buzzwords like "protection" "freedom" or "safety" into a bill, there's usually an ulterior motive that runs counter to those ideals.

You're not wrapping them tight enough if a 3 week old is able to squirm out. Work on making it tighter and making sure you really tuck it underneath them with the last wrap and they should be unable to work their way loose.

I'd call in a separate roofer for an opinion. There are some large gaps in your sheathing where you can see the weather wrap through, and boards that have obvious signs of water damage they left in place. I would want someone else to take a look at this and confirm it's done right.

I’m trying to decide whether this weekend we should buy and assemble a smoker!

If it's in the budget, then do it! Sounds like a fun weekend all around.

coaching+anxiety can be a rough pair

Introvert here, I totally get that! Sorry you're missing the softball game, hopefully you can catch the next one.