The Dutchman would be probably be a bit easier for you; you may have to get full battens (on the lowers) and look at some attachment "batt slides" -- but with those I essentially can single hand with an autopilot.

The Lazy Jack (really a Harken, simple variation) worked fine with our previous boat. That was a Sabre 42 with a somewhat larger main than you have on your Island Packet. That worked fine too -- but we had full battens and eventually opted for batt slides to make dropping the sail easier.

Rolling up the main, in either an in-mast or in-boom situation really is (as others have said) going to entail a lot of money for you Craig. I think I'd try the lazy jacks first (because they're really simple to install if you use a Harken "kit") If they work for you, then I'd go from there.

Docking is something that you'll then have to deal with. If your wife is good with piloting you in, then I think you have a decent shot -- if you have to depend on her to fend-off, pull lines, etc., then I'd not think that's as good a plan if her back/neck/etc. is giving her fits.