Surprised no one has commented. Honestly, IMHO with the right weather windows, etc... I'd think so. Sail handling systems, I'd want a simple set of lazy jacks and think through storm sails (jibs in particular), some sort of non-electronic self-steering gear, and a cruising spinnaker. In this day and age you can also get an AIS/VHF in one package for around $300. How old is the running and standing rigging? Condition? Are they on tap for replacing, or has this been dealt with already? How about the boom and the goose neck? Is the traveller easy to use and main sheeting system easy to handle under load? Do you like all your halyard locations and reef line access for short and single handing? How about anchoring and ground tackle? Seems like you have the boat prep part of the equation pretty well in hand. The bigger question is about preparation of the sailor. Take no offense as none is intended, but most boats are far far tougher than their humans.