I would recommend getting your boat ready to live an anchor
first. You can get it ready to cross oceans later. That way you can enjoy living at anchor
soon. You can spend lots of time doing that in the next 3-5 years, and then get it ready to cross oceans in the year before you leave. For me, that would mean:
Engel - get this first
Battery Bank - if you have two good batteries, you are probably fine. If not, make this a priority. Also if you do not have a good alternator, make this a priority.
Radar - if you have lots of fog
in your area, do this soon. If not, wait.
- whenever you can afford it
- wait until you are ready to leave if you will just be weekending on your boat
Windvane self steering
- since you already have autopilot, wait and keep a look out for a sweet deal on a new or used one. No need to get one until you are near ready to leave
Water Maker - wait until just before you leave