Hmm, very interesting sammy and what grouse looking kettle!

So, how much?
I myself am not a fan of the sight glass, unless you calibrate them they don't really tell you all that much*. There's no real harm in them per se, however you do mention chilling in- kettle and at that point the combination of a potential infection source and cooled wort becomes concerning to me. If your sanitation process is up to scratch then there should be no problems, however I would be very particular about it, I have heard of some brewers finding accumulations of muck upon completely tearing down their tap &/or pickup- outfitted kettle, and don't think a sight glass would be exempt. that's bearing in mind that that area may not be quite as hot as the rest of the kettle, then relying on heat reaching every nook and cranny to sanitise could be optimistic. If you're prepared to strip the tap and sight glass down every time, it should be fine though.
* That's coming from the Maxi-BIAB point of view where many of the measures are 'about 2/3', 'full to the brim' etc, but deliberately so.
WRT
Venturi effect, I doubt it I'm afraid. There's a lot of physical head (the column of wort in the sight tube) and then a little bit of head loss to friction (from the narrower bore sight tube) to overcome before you get air being sucked down into the wort stream, at least initially, but perhaps at the end you may see some. I haven't worked any of it out, but at the velocities the wort drains out the tap by gravity, I would be surprised if it did introduce much, if any at all. Nice idea though, that's actually food for thought WRT wort aeration.
