Nothing I do on the -200F Freighter gets the winglets.
On the -200, I have to manually edit the aircraft.cfg file.

Here is the 727-200 Air Canada variant without the changes:

[fltsim.0]
title=CS 727-200 Captain Paint0
sim=cs727200
model=
panel=
sound=
texture=aircanada
kb_checklists=
kb_reference=
atc_id=C-GYNM
atc_airline=Air Canada
atc_flight_number=722
ui_manufacturer=Boeing
ui_type=727-200
ui_variation=Air Canada
ui_typerole=Commercial Airliner
ui_createdby=Captain Sim
description=727 Captain (727-200 Expansion Model) v2.4\n(c) 2010 Captain Sim www.captainsim.com  
visual_damage=1

and with the changes:

[fltsim.0]
title=CS 727-200 Captain Paint0
sim=cs727200
model=another company
panel=
sound=
texture=aircanada
kb_checklists=
kb_reference=
atc_id=C-GYNM
atc_airline=Air Canada
atc_flight_number=722
ui_manufacturer=Boeing
ui_type=727-200
ui_variation=Air Canada
ui_typerole=Commercial Airliner
ui_createdby=Captain Sim
description=727 Captain (727-200 Expansion Model) v2.4\n(c) 2010 Captain Sim www.captainsim.com  
visual_damage=1

Hope this helps.