To me, it sounds like your dissatisfaction with the FE dipstick design is misplaced, seems the issue is due to aftermarket bracketry, rather than any problem with the factory design. On my 59, I have a Canton 7qt. oil pan, a factory J windage tray, and a replacement CJ dipstick and tube from Tony D Branda. To make the dipstick clear the windage tray required just a minor bend at the end of the dipstick, so when I install the dipstick, it misses the tray. I suppose that you could remove the cast iron dipstick mounting housing, from either a FE 4x4 rear sump pan, or maybe a 5.0 FOX Mustang pan, and install it into the FE pan, in an appropriate location, and use the matching dipstick and tube. These brackets are riveted to the oil pan, with a cork gasket. Also, I can`t see why a deep sump oil pan would be an issue with headers, unless you are planing on using a wide, road race type pan. I have used 9 quart front sump pans on a couple of Fairlanes and Mustangs, using either Hooker or Cyclone headers, and there was plenty of room between the oil pan and headers.