Hi Tacker
If you want to pay someone to sail it down I was talking to John at Boat Sales Tas a few weeks ago and he mentioned that they knew a bloke who delivered boats for them
John said he did a good job, looked after the boat and was not all that expensive
If you are interested it might be worth giving them a call
www.boatsalestas.com.au/contact/I reckon it would work out less than trucking it over
A mate of mine has sailed a 27 footer and a 32 footer from Sydney to Port Huon over the last couple of years and years ago he sailed a 24 footer back single handed from Airlie Beach in short hops along the coast and has not had any major drama's and enjoyed the trip but i think the main thing is to give yourself enough time to allow for bad weather
If you ask around the clubs in Hobart you might find someone interested in doing the trip with you
Regards Don