I ended my recent stay with one night at the DLH and booked a preferred view room, due to construction concerns. I received a DTD view in the Adventure tower and it was beautiful. IMO, if you're not big into a room with a view and since most or all of the construction will be wrapped up by your arrival, I wouldn't sweat it. All the rooms are done and the atmosphere of the hotel is really coming together. The rooms to me, just shout you're at
Disneyland and are beyond cool. I have stayed at a lot of themed deluxe hotels at WDW through out the years and the Disneyland Hotel is now one of my favorite places to stay. I will stay there when at DLR from now on. My tower preference is the Adventure tower and that's what I will request when booking in the future.
As for the free upgrade on check in, I wouldn't count on it.
IMHO for convenience, request a room in the new Fantasy Tower which houses all the restaurants, one side overlooks the pool, the other side the entrance of the hotel. They are currently working on the final details outside the tower facing the entrance, painting, landscaping, but I noticed people were in the rooms. The remaining work on the pool should be finished by then, but as always, please contact Disney and be sure to check. What I'm telling you is what I heard from the staff this past Friday.
You just can't go wrong with staying there in any of the 3 towers and enjoy your trip.