That's a nice and large Romania right there. In this situation where Romania isn't able to grab the Greek Islands or force a surrender, I would expect either the Italians or the British to take control of the Islands before your new transports are ready for action. Both nations have a powerful navy in the Med, and thus the capability to take the Islands. Not going for them, while avoiding the other major player, would give Romania the possibility to dominate that side of the med, isolating Cyprus in the process. I would expect both Italy and the UK are trying very hard to grab them through diplomatic means, and if that fails, that both are rapidly preparing to take them by force. With all it's conquests Romania is becoming a serious regional player on land. With the greek Islands, Romania will become a regional player at sea as well, if only to protect those Islands and the trade routes between the mainland and them. What makes it more interesting is that there's a timer on this, if neither the UK nor Italy get hold of the Islands within ca. 2 months, Romania will take them.
Will they prove inept at resolving this? At this point I'd expect Italy to declare war on Greece and to rush those Islands before the British have time to react. Their entire Balkan plan has already been foiled by Romania, I'm sure they're chomping at the bit to get some territory now, and Crete and Mythiléné are relatively easy targets for the Regia Marina, especially when you consider that most of the Greek army is sitting in Romanian POW camps. Of course they might be scared of the British, but considering how much they've already given in to the Germans with the Anschluss, the British would probably not start WW2 proper when faced with the fait accompli of Italian troops in Crete.
I expect the British to try and get the Greek government on their side, and for them to accept Romanian terms for the mainland, and for Romania to accept a British presence on Crete, to make sure the Islands don't fall into Axis hands, even if Romania joins said Axis. This in exchange for British pressure on the Greek government to give in to Romanian terms, and allowing Romania to avoid a potentially costly naval invasion (without Marines, Landing Craft, or significant Naval gunfire support). All behind closed doors of course, they wouldn't want to offend the Axis after all...
Will they prove inept at resolving this? At this point I'd expect Italy to declare war on Greece and to rush those Islands before the British have time to react. Their entire Balkan plan has already been foiled by Romania, I'm sure they're chomping at the bit to get some territory now, and Crete and Mythiléné are relatively easy targets for the Regia Marina, especially when you consider that most of the Greek army is sitting in Romanian POW camps. Of course they might be scared of the British, but considering how much they've already given in to the Germans with the Anschluss, the British would probably not start WW2 proper when faced with the fait accompli of Italian troops in Crete.
I expect the British to try and get the Greek government on their side, and for them to accept Romanian terms for the mainland, and for Romania to accept a British presence on Crete, to make sure the Islands don't fall into Axis hands, even if Romania joins said Axis. This in exchange for British pressure on the Greek government to give in to Romanian terms, and allowing Romania to avoid a potentially costly naval invasion (without Marines, Landing Craft, or significant Naval gunfire support). All behind closed doors of course, they wouldn't want to offend the Axis after all...