do "free upgrades" ever happen?

No, the dedicated 1 bedrooms on the green are Boardwalk view, at least 5051 is certainly. Likely they use it as a swing room as there have been reports over the years of people receiving it booking either category.
I think it is P/G view. We had 4th floor studio below and it was booked P/G view. And that 4th floor 1BR is listed as P/G view as are all the studios next to it and all the same studios on the 5th floor. Same with all those on 3rd floor. On Touring Plans. They just have that 5th floor 1BR as BW view and I think it's incorrect. I have noticed they have many rooms mislabeled.
 
Member since 2010, 15 DVC trips so far. One upgrade in 2016, BLT 2 BR Standard to BLT 2 BR Lake View. It was awesome. At this point, I considered getting our room early is an upgrade!!
 
I think it is P/G view. We had 4th floor studio below and it was booked P/G view. And that 4th floor 1BR is listed as P/G view as are all the studios next to it and all the same studios on the 5th floor. Same with all those on 3rd floor. On Touring Plans. They just have that 5th floor 1BR as BW view and I think it's incorrect. I have noticed they have many rooms mislabeled.

I have booked boardwalk view and received 5051, this was in '07 (I posted about it at the time on the MO board). This is why I am arguing that it is a bw view room or used as a swing room.
 
We have been upgraded 3 times since 2010.

The first two times were late arrival nights for us at boardwalk for race weekends. We had standard studios reserved.

I went to the desk and they could not find our reservation. It had also disappeared from the website. CM disappeared for a bit and came back and told us that the reason it disappeared was because we were upgraded to club level at boardwalk inn. I didn’t bother to ask why.

Second time was similar. Studio to club room at boardwalk inn.

These were both shorter stays. 3 to 4 days if I recall.

Maybe some won’t feel that the studio to a regular room with club is an upgrade but we loved it!! Side bonus was two full queen beds!

Third time was morning arrival. The room was taking a while. When I asked for any ready room The CM said.....you’re going to be happy. Just wait until the room is ready. We had booked a one bedroom standard and were upgraded to one bedroom boardwalk view. That was amazing!!
 

In 16yrs of ownership at bwv this was the first year I got something I didn't book. I booked a standard view 1br and got a 1br overlooking the village green. Technically that room is boardwalk view.

This was a 4 day trip in July. I'd never expect that to happen during a busy time like the fall.
That is P/G view.
I have booked boardwalk view and received 5051, this was in '07 (I posted about it at the time on the MO board). This is why I am arguing that it is a bw view room or used as a swing room.
And I think it was originally classed as BW view but caused so many complaints that the category was changed to P/G.
 










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