You might come up short if you're wrapping a really wide bar, like Noodle 46's, and your spacing is tight, but generally on drop bars one roll should fit each side. Also, it depends on whose tape, of course, some are longer rolls than others. In general, I always have leftover bits. Sometimes I'll use a bunch of leftover bits to make a mixed-color wrap for fun or temporary purposes.
When I wrap drop bars I do separate wraps of the tops and bottoms, both ending up at the brake lever. If the brake lever allows for it, I wrap with the clamp in place but the brake lever removed, then the brake lever holds the tape ends in place. Otherwise, the tape goes up the side of the lever body and the brake hood covers it up.
For spacing, I go for 1/4-1/3 overlap on the straight parts. I use the angles of the weave (in cotton tape) to judge it. On the curves, it's 1/2 overlap on the inside of the curve and just a smidge of overlap on the outside. If you are using tape that doesn't have adhesive on it, you may need more overlap.
Also, FWIW, I have started wrapping the entire bar with electricians tape to hold cables in place. Newbaum's comes off of electricians tape way easier than it does off raw aluminum, making fresh wrap a much less time consuming job.
Ted Durant
Milwaukee WI USA