It is sometimes said that the handicapper is doing a good job when the crews of all boats are equally aggrieved about their handicaps. We will say no more.
The handicapping system used by TSPYC is based on past performance (rather than the design/dimensions of the boat or its theoretical speed). Thus two similar boats could potentially have different time correction factors; or conversely, two very different boats could have time correction factors that are very close. Time correction factors are adjusted periodically in pursuit of an elusive handicapping nirvana whereby all boats would have finished simultaneously on corrected time. Like all forms of nirvana, this is not impossible but exceedingly rare.
The best way to improve your boat's placing on handicap is to sail the course faster than you have done in the past. Attention to sail trim, crew weight/position on the boat and taking advantage of windshifts are three areas where gains can potentially be made. In contrast, if you are well back at the start line, spend time sitting in another boat's dirty air, do not carry a spinnaker when you have customarily done so, or your boat has growth built up on the underwater surfaces, this will show through in the handicap results.
TSPYC's most recent adjustment of race time correction factors took effect from 4 September 2011 following the 2011 Winter Series and took into account the previous 10 races. Previous and new handicaps are shown below - the "difference" column shows how many minutes per hour of racing the time correction factor gives a boat, as compared against the scratch boat.