The air loss from the whip is minimal. The hole inside is tiny. Not sure how much air would be saved with a 10" whip vs a 24". I would find it difficult to fill my gun with a 10" whip in the field.
The point at which you would refill your gun is up to you and is usually the point where velocity / accuracy starts to fall off, or just above your regulator pressure if your gun has one. But, the fill point won't change how long the air in your tank will last other than the small amount of air lost when you disconnect the gun from the tank. If you don't need to lug the tank around, then get the biggest tank to get the most fills. If you want to carry the tank in a backpack, then a 90 cubic inch tank might wear you down faster than a 45 cubic inch. Assuming the air in your tank is dry (which it really must be or you will be ruining your tank), don't use any inline filters when filling from the tank. They waste quite a bit of air each time you bleed them.
On your calculations, you might be entering the data incorrectly. This is what I am getting with these numbers:
68 cubic inch tank
Starting at 4500 PSI
Filling airgun to 3600 PSI
Refilling airgun at 2600 PSI
450 CC bottle
----------------------
12.6 Fills
Same numbers but with a 90 cubic inch tank = 16.7 fills.
If your gun still shoots well at 2200 PSI, then you can wait until then to refill it. You will get 11.9 fills from 2200 PSI with a 90 cubic inch tank, but the number of shots from your gun between a 2600 PSI refill point and a 2200 PSI refill point to 3600 PSI each time until your tank runs dry will be roughly the same.