If U R still tuned in to this post.... Nice plan .... what a great read - well done seabreezers....
Can't repeat this one enough the mechanics...
Might be wrong - but if it is a 2nd hand buy then..
Get your motor / drive serviced / overhauled + battery/electrics checked (or DIY if U can). Understand your motor - if it bails do you loose the boat??
Hopefully U can unplug a fuel line / cooling line - ditch water from the fuel trap, find a loose lead, basically you are familiar with it...
Years back - Dad's mate had similar bit bigger wooden internal chug chug (diesel) - he had added tap to his inlet cooling pipe and ran a hose to a sieve filter in the bilge - any time he wanted to he pumped the bilge dry by sucking it using the motor's cooling pump - U could see the trouble if you sucked the bilge dry and did not flick the tap back - but U could have an alternate automated float setup.. Great rough weather pump.
Make a sea anchor - if for no other reason you understand how to use one.
Stuffed if I know why someone red thumbed JBShack when his post first went up - what an offer - take it up..
When all is said and done the Lighthouse to Leightons still runs across there..
so do what they do - tick all the boxes...
If you do not have enough knowledge about weather forecasts - talk to JBShack.
1) the weather = go / no go (U or JBShack / safety people)
2) Planning for safety = understand + ticked the box = go / no go (Read posts above - lots of experience)
3) the motor = go / runs but not for long enough (Buck stops with U).
3 go's & U should have a ball - use the same criteria before return trip - and U will be doing many more...


Cheers
AP