Welcome to the forum! Yes, sadly it's pretty quiet around here but still better than FaceBook:)
1) Quickshift: Yes! It is easy and I HIGHLY recommend it. It is NOT the buttery upshift of an electronically controlled ride-by-wire, and it will no 'blip' or downshift for the same reason. It is meant to power up-shift near redline. Ya it should help 1/4 mile times slightly, no one is using a clutch for that anyway.
You can DIY a DynoJet #103 linear sensor (IIRC) as the OE ECM is up to the task by simply enabling the function with ECMDroid, ECMSpy, TunerPro etc. Also plenty of types of bolt on kits available, check out Rev-Mo.com
2) No it is absolutely NOT 'harder on gears' .Your transmission is called a constant mesh transmission. Might be a fun thing for you to geek out on You Tube about.
3) You'll need both pulleys and a belt, not worth the expense IMO, a chain conversion would get you any ratio you wish. Probably cost less too.
4)Yes changing final drive ratios will change the speedo as the sensor is on the transmission output, not the rear wheel. You can either CR dash/calibrate/ or switch the guage pack to a GPS based aftermarket one.
5) I'm all for DIY, But theres lots of CF goodies to be had out there already. I LOVE the CR done by Speed-of-color. https://tekarbon.com/collections/buell/model_ebr https://www.motocomposites.com/categ.../1125r-cr.html https://speed-of-color.de/buell-parts-xb https://mdicarbonfiber.com/collections/buell/1125 https://www.bestemusa.com/XB12_c_44.html https://www.twinmotorcycles.nl/websh...p?mc=1&cid=288 https://bottpower.com/buell-custom/buell-parts/
lots of less quality things on e-bay as well, YMMV
6) IMO for street riding in those temps, stick with the 20w-50 API "V-Twin specific" oil in any brand or synth you want. I would do track days on my CR in 43C days in Florida and use 60W for that extreme example, but thats pretty extreme. The valve train is always gonna rattle like that.
7) Ohlins will have a recipe for that already, just call and order. Wilburs does too. IMO any serious suspension upgrade for track use and you might just be swapping on a front end anyway so keep that in mind. There are tricks to keep that front brake effective and cool, but only up to a point.