Usually the first week in April is when I transfer all the wine into my 3 gal carboys. By then the wine is clear and has developed nearly full flavor. I dislike 5s because they're heavy and unwieldy. Three gallons makes 15 bottles... plenty even if you're having a gathering.
As with everything else in my process, my bottling station is also gravity based. When I was first introduced to wine making back in 2005, the Italian men teaching me used just a hose and a thumb...no funnels... wine everywhere. I said nothing but my background in retail hardware had my wheels turning from day one. Vinyl tubing ziptied to an aluminum arrow shaft or fiberglass rod along with a ball valve and a few adapters had my teachers amazed, and I'm pretty sure I moved up a few rungs on their respect ladder that day.
I designed my bottling bench after trying different heights for siphoning, and in the end came up with this setup that has served me well for many vintages since my humble beginnings in 2006. The wine room of today was pretty much built around it.
This past summer we visited Copper Fox Distillery in Williamsburg, VA, where staff actually does the labeling by hand. I was intrigued by the gadget they had built. Theirs is back-lit for final clarity control.
Blessed be... and happy wine making!