I would say that on the 24s, Congleton, JB, Stretton not above 1500 wouldn't cause
me as many headaches as Spiney aludes to and I would happily do it. It is, after all, only Class D airspace and standard radar or vertical separation is not necessary.
I would, however, agree that you would be identified to the Tower Departure controller and he would "miss" you with the departures, probably without resorting to non-standard departures or a "check".
Coming any closer in, ie via Knutsford or up the M6 like the Police tend to do, now thats a different matter!
Ask and you might get, but if you have to wait 5 minutes to get in on the radio, then best not to ask!
Edited to add: Make sure you're not above 1250 just after JB since Liverpool inbounds fly at 1800 QNH over the Low Level Route!
All the best...