Bragging rights? eh, kinda? sheer power... absolutely IMHO.
If you value acceleration, get the Plaid. Reading your responses a bit, I think you are of the mindset. The Plaid will not disappoint.
I have never had anyone say "wow, a Model S!" but when we are talking cars, and I mention Plaid, typically at work, talking about cars (I work with a lot of tech-types/gear heads)... someone always goes "wait, legit Plaid? and the room gets educated by them on the Plaid, I don't normally need to say much. My boss owns a Mclaren, we share roadway stories and dragstrip tales. I don't know if that would be as entertaining if I had a base model. Also, in a room full of engineers, the "symphony of engineering genius" that is the Model S Plaid comes up in conversation. I enjoy those chats and being able to participate first-hand. If you do too? don't cut it at the base MS.
I also recommend Enhanced Auto Pilot. When you are talking a $100k car, $6k is a drop in the bucket for a car that can now change lanes, NOA, be summoned, and park itself. Yeah... a bit of a parlor trick at times, but there are functional reasons for all of the above (like someone parking too close). I purchased EAP, and I love it.
I think, if the budget can manage it (be responsible of course) you can never regret getting the Plaid. If you get a base model, you will always be wondering... what if I had.
My 2 cents, GL friend!