Its such a shame you cannot still "promote threads" in rank!........we need more fun.
I can't get the fifth sidewinder in my Callipygian.
I suspect that's because the hull mass is 25 tonnes per sidewinder, but when kitted out (even D-rated) it's a little more.
And now I need to a good curry to dislodge them.
http://i.imgur.com/v2DG4lr.jpg
You should probably ask a high ranking Federation officer.
Start with a Rear Admiral
I don't think fitting a Sidewinder in an Asp would be a problem:
http://vinnykumar.com/wp-content/uploads/2011/06/xlarge_carincar.jpg
You might want to check out the official ingame description of the Anaconda.
The Anaconda is the pride of Faulcon deLacy's ship yards. The design was first manufactured in 2856 by RimLiner Galactic. After numerous mergers the template was eventually owned by Faulcon deLacy, who have made only minor changes to the classic design. The Anaconda is a versatile craft that can transport large cargos as well as pack a decent punch. Some smaller navies use the Anaconda in the light cruiser and frigate roles. The Anaconda can also be upgraded with a docking bay allowing small fighters up to Sidewinder size to be carried and launched.
That depends entirely on the cargo bay architecture. You might be able to haul multiple Sideys in raw tonnage, but the Asp might not have the kit to put in a docking bay for a fully-assembled ship.
I bet my Asp would break if we tried fitting a hauler in it, let alone a hauler with a Sidewinder in it.