Thanks these are great questions and congrats on your over-wintering and splits.    I will try to share my experience.

1. The smoke certainly can condense on the uncapped honey in the super, but I have been using smoke from below and on the main brood box without trouble,  If most of the honey  cells are capped then you should not have contamination.  The takeaway: I smoke at the entrance and a little on the brood box, but not the super directly and it has worked well for me.

2. Dr. Seeley may use both 10 and 8 frame boxes and google shows many beekeepers overwinter with 8-frame medium's (6 5/8" frames) and I think our expert beekeeper Steve Gomes overwinters 8-frame mediums.  

3.  You can clean the tools with alcohol.  I use ever clear (ethanol), but I think isopropyl works well too.  You likely can use petroleum distillates, but you should wash in soap and water after.  Jeff Clark had guidance for the gloves that I have yet to try.  He says, to  buy one size too small of leather gloves then put them on a wash your gloved hands.    I think you could do this with the solvent followed by hand soap and water.  I have not tried it, but my gloves are due for a wash.  For stubborn propolis on the hive tools, I would resort to bar-keepers friend and a synthetic steel wool that is an all-powerful cleaner.  Regarding the gloves,  Dr. Seeley recommend  these long 12" Ansell 5mil  nytrile gloves at our meeting a few months ago:

https://www.amazon.com/dp/B003K15DJE/?coliid=I1D7POKNNR3ZVU&colid=1IXSDER6B7X&psc=0&ref_=lv_ov_lig_dp_it

He says he re-uses them until he cannot use them again.

I hope this helps, I I expect Jeff and Steve to chime in.

-Eddie