This is a problem I too have been working on. I don't have a good answer. Choices include:
1. Sailing it back myself. Add another 30+ days. How will I feel about turning around and doing the same thing again, after three weeks at sea?
2. Paying someone else to sail it back. My sailing instructor in Sasualito said his day rate (the instructor and one crew) was $500 plus expenses. 25 days * $500 = $12,500 Add a couple of plane tickets and provisions. Maybe $15k all in?
3. Ship it back. Here's video of the seminar that the SSS just held on the topic.
I spent some time before Christmas on the phone with a guy in Hawaii trying to price this up. I wound up with a range of $15-20K for a 32' boat. If you go with one of the races (or can be treated to the racer 'group' pricing you do better. It's still very expensive and that does not include shipyard work at home to re-step your mast etc. Worth it if you have a $175K carbon racing rig. For my $30k '90?.....
4. Sell it in Hawaii. Pricing doesn't seem to be terrible in HI for boat sellers, but who knows how long it will take to sell etc. Plus by the time you sail your boat to HI, you probably love the boat a lot, and just puking it to someone else doesn't seem fair.
5. Keep the boat in HI over a year and bring it back the next summer?...
My wife doesn't like #1 or #5 - expensive in time. All of the other ones are expensive in money.
$.02,