We have cruised west to eastern med for the past 3 summers in a 42 foot cat. There are places particularly near charter
hubs where you will stuggle to find a double berth unless you book ahead (and even then certain days will be a block out) so you do have to be a bit more forward planning than monos at times especially in the areas where all weather anchorages
are rare eg mainland coasts of gulf de lyon.
The flip side of course is a rolly anchorage is less of a concern on a cat.
Yes there are quite a few places where lee winds can behave oddly (another one is the straight of messina) and you will hear plenty of stories from other cruisers but it wont take long to learn to reef early in such parts
We were a bit disenchanted with the mooring
aspects in the western med in a cat due to harder to find berths, less all weather anchorages
(combined with dodgey weather forecasts) and truly crazy prices once they are doubled in the high season but dont let that put you off - as you travel east it gets better and better.
has plenty of cat friendly yards with Preveza a standout for us. I would look at that as your winter option if you are leaving the boat midpoint. Turkey
has brilliant facilities but you are back to double charging
for cats at times, even on land.
A good primary anchor is indeed essential and there are quite a few places where we have had to anchor in 20m plus meters but not too often. (often its with a long line ashore and a steeply sloping ground so even 2 1/2 to 1 is ok) Our 60m of chain has been sufficient and honestly 100 seems overkill to me but we dont have a high windage cat. Yet to use the kedge in 3 years here as you will usually opt for the long long line.
Yes its a bit harder and more expensive to do parts
of the med in a cat vs a mono but its still completely doable and the difficulty is more than made up for by the unique cruising that is the med so dont let it put you off at all.