FFF, I disagree with this: I would argue that in my scenario, (a) comes into account, because it is necessary to fly below 1000' in order to land.
Under what rules are you flying/landing? VFR or IFR? I can't see how you legally transitioned from one (IFR) to the other (VFR).
Evo, How high does the cloudbase need to be for me to land? At least 1000' above any obstacles within 5nm of track.
So, approaching Goodwood in the conditions you describe (1500' base) you can descend over the sea to VMC and commit to landing VFR (circuit/standard VFR join whatever)
Remember cloud ceiling (in METARS/ RT) is AAL or AGL, not AMSL.