In my case, I had requested 10 specific Boardwalk View 1-bedroom villas that had the fully enclosed and private balconies. Out of 30 total 1-bedrooms, my chances were about 1/3. 3 of the other times were garden/pool view, so out of a possible 188 room matches, the odds were much lower to get one of my specific rooms. I don't specify dedicated vs connecting.
I think the two times I didn't get a specific room request was just down to odds/availability - when I checked in, those room numbers were already booked. But I was able to get 2nd general area requests both times - croquet lawn area which I prefer over the pools. So request-wise, I'd say close to 100% lately, but regarding the specific room number requests, still pretty good.
I had room 2039 this time - my 4th time staying in that room (I have gotten 2011 5 times). The thing I like about those rooms is probably what some others dislike - the huge covered and enclosed balcony - because it doesn't have a rail-type balcony, you don't see the Boardwalk if you're sitting in a chair - to see the full view you have to be standing at the end of the balcony (or do what I do - bring one of the kitchen bar stools out on the balcony and sit right along the rail with a drink on the nice, side ledge - it's like sitting at a bar overlooking the lake - great for people-watching, fireworks, etc. The balcony is 3x larger than any of the regular open balconies, and you can sit out there in pouring rain or lightning.
Plus, 2039 is only about 1/2 way down the hall, so it's nice not being as far from the lobby area. The ice machine was just 2 rooms away which was perfect - and being on the 2nd floor meant no elevators needed walking from the lobby area. And there's a nice staircase that few people seem to know about that's right in the 'bend' of the hall where there's the little cut-out from the floors above - that stairs takes you down to the boardwalk level right between the gallery and general store - so you don't have to go all the way to the lobby or elevators when leaving, especially if you're planning on hitting the Boardwalk, walking to Epcot, or grabbing the boats.