trip planning

I'm getting closer to booking tickets for a trip next May (yes, 9 months in advance*) and I'm having trouble making some key decisions. They are not all mine to make, but even the conversations with Mr. Squirrel are more confusing than not.

We have the following options for places to fly into:
Munich
Budapest
Vienna

And the following options to fly out of:
Sofia
Bucharest

I just found a flight that goes: ("our little city" - JFK - Amsterdam - Munich) then (Bucharest - Rome - JFK - our little city) for $850 rt. Seriously. What this does is throw a city I'm dying to go to back into the mix: Ljubljana. We would end up spending two nights in Munich, two in Ljubljana, and then taking the train into Croatia as planned... this seems to work out better than flying into Budapest (as originally planned) and then taking the overnight train to Zagreb.

Unfortunately, the flight I was counting on from Split (Croatia) to Sofia seems to no longer exist. This is bad in some ways and good in others: we were going to have to drive back from Kotor (Montenegro) to Split for that flight... a good 4 or 5 hours, I think. Now, we'll probably fly Dubrovnik - Vienna - Sofia, thanks to low-cost European airlines.

*Note that the reason I'm planning all this so far in advance is two-fold. First, if we buy the plane tickets NOW, there's less chance of not having money later. Our Rome trip was canceled for lack of funds, and I'd rather not have that happen again. Second, it's a long trip and I need the planning time to make it all work in my OCD-tainted head.