Prediction of products in reaction of dicarbonyl with alpha-haloketone
As you've already figured out, cyclohexane-1,3-dione is more acidic than chloroacetaldehyde, the pKa of the diketone in water should be around 5.3.
The enolate of 1 (sorry for the circle in the structure, i'm to lazy to fix it) and 2 undergo an aldol reaction yielding 3. With a bit of charge shifting, we get again a nicely stabilized enolate (4), which dehalogenates (you might call that an O-alkylation as well) to 5. Subsequent elimination under aqueous conditions results in the formation of 6. I'd say this is, more or less, an example of the Feist-Bénary reaction.



Btw, I created the drawings with BKChem.

A conceivable depiction for the "transformation" of 3 to 4 is given below, but please note that this is just a model to please our eyes and minds ;)