I can't tell you how to make your strings longer. The strings i use need about 2" cut off to wind to the bottom of the post with vintage tuners.I use d'Addario EXL-110 strings. On my Tele with vintage tuners I don't cut the high E string -- I just stick it into the hole and wind the entire string onto the post to prevent slippage -- and it never gets anywhere near the bottom of the post. Is there a special technique to accomplish this, or does it require extra-long strings?
What I CAN tell you is, what people think is stretch when breaking in a new set of strings is negligible. It's the strings seating on the post, and the fewer windings you have, the faster your strings will "break in" and there will be no loss of tuning stability.
2 winds on a wound string and 3 on plain strings is plenty.
The only benefit to more windings is when trying to get more break angle at the nut.