For a long downwind race where I may need the same sail for extended periods, how do I make sure I have redundancy in the sweet spot of my asymmetric inventory?
For Transpac, and many other coastal and offshore races, the A2 spinnaker is your workhorse. But the A2 you use for inshore buoy races to sail at low angles may not be the best sail for offshore racing, when surfing waves and dealing with shorthanded sail changes. For the Reichel/Pugh 45 Criminal Mischief, we developed an A2.5, which is essentially the same size as an A2, but is much more durable. It has more reinforcement, a flatter luff, a twisted leech profile, and an oversized tack patch. This kite bridges that important gap between the A2 for flatter seas and lower angles and the smaller A4 for higher winds. This allows us to drive the boat harder in those crossover conditions, when we need to be able to put the bow up to track waves and not risk a wipeout due to the size and fullness of the inshore A2. This also allows us to sail with two A2s (A2 & A2.5) that are each efficient in a given wind range. If we break one, we still have one with which to finish the race.

I race a Beneteau 44.7 in local PHRF events. The boat has a racing main, a 145-percent genoa, a 100-percent jib, and an all-purpose spinnaker. I’m planning to do the Bermuda Race but have a limited budget. What essential sails would you recommend I add to my inventory?
A 145-percent jib top, heavy genoa staysail, and reaching spinnaker would be the primary sails to focus on. There can be a fair bit of reaching in the Bermuda Race and the jib top is a potent weapon for true-wind angles between 50 to 110 degrees. The jib top offers considerably better performance in this range because the design is orientated to reaching. It also makes the boat easier to drive and more balanced, especially when paired with a genoa staysail. The genoa staysail is an extremely versatile sail that can be flown inside of headsails and spinnakers; in a seaway it can help settle the boat into balance.  You should also have a spinnaker for tighter reaching angles of 100 to 145 degrees, and for better control when sailing downwind in high wind speeds. This sail will be significantly flatter than your AP spinnaker and should be made of 1.5-ounce cloth.

I’m racing my Baltic 37 in the Pacific Cup and I have three full-size symmetric kites. My boat has problems tight reaching, and we have control problems downwind in anything above 18 knots. Is there a sail that can help alleviate these problems?
Because your boat is a heavier IOR-influenced design with a masthead rig and overlapping genoas, I would eliminate the symmetric spinnakers. Asymmetric spinnakers are more versatile and user-friendly offshore, especially in surfing conditions when the acceleration brings the apparent wind forward. I would first add an A3 or A5 reacher, which can also serve as a heavy-air running kite to 150 degrees, and a light-air reaching kite, which you can carry as high as 90 degrees true-wind angle. Its primary intended range is the transition zone between your jib top and your full-sized spinnakers.

An A2 or A4 runner would have the same sail area as your biggest symmetric spinnaker, but provide a better option to bridge the gap between 130 degrees and 160 degrees true-wind angle. This would also provide better control running downwind in the 16- to 24-knot range with waves. Above this range you’re back to the A5, with the reduced girths and smaller sail area to allow you to sail a bit higher true-wind angle to maintain a user-friendly groove to drive the boat around in the waves.