Do you want a project boat or do you want a turn-key sailboat ready for adventure?
Project Boat
If you choose a project boat you need to be savvy across all disciplines – diesel, electrical (12v + 110v), rigging, navigation/communications and general boat repair (fiberglass/epoxy repairs) – and have a large arsenal of tools (this is also true if you are planning a passage)
You also need to have the time, access to a boatyard/lift that let owners do their own work and a budget commiserate with proposed upgrades. Once these items are in place, multiply this budget by 2 and you will be in the neighborhood. If you choose a project boat and you are not qualified to do the work costs will skyrocket and quality will most likely suffer.
If you plan to hire out all of the work, get estimates and multiply by 2 – maybe more – and plan accordingly.
Ready to go boat
A boat that is ready for adventure will have the major systems upgraded and good documentation for making repairs and maintaining systems. All that will be needed is your personal touches but nothing major.
Your time will be spent getting to know the boat and sailing, not fixing, repairing and sitting at dock.
You will pay more for this boat but be getting all of the upgrades and work for 25 cents on the dollar. That loosely equates to a $20k purchase premium gets you ~$60k+ in upgrades.
When making this decision, make sure your partner and crew are onboard with the decision.
If you choose a project boat (any boat with no significant upgrades in the past 20 years) you will be tearing the boat apart stem to stern fixing, repairing, maintaining and upgrading. Even the smallest upgrade will displace crew for days, hours and weeks. The 1-hour project turns into 12, then 48 followed by a set of ‘might-as-wells’ that push your voyage out another 2 months. While this can happen on any boat, make sure everyone has the same expectations and stay in alignment.