When referring to with jacket or without jacket, is this bare copper or with insulation for the purpose of the number of conductors in a trade sized conduit?

USEI conductors are jacketed. Single conductor wire used to have a cloth jacket.

On a similar topic, Table 6 is for stranded conductors. Solid conductors are a little smaller but you can always use Table 6. It's the worst-case measurement.

When you need to push it, you can use the manufacturers measurements and when you really need to push it, you can measure the wire and the conduit.

Here are some tables using the manufacturer's specs: http://www.codemath.com/cgi-bin/Run.pl?script=FillTbls

i'll go one better. have'nt you heard the question, how many wires can you pull into a conduit? answer is, how big is the gorilla on the fishtape. had to throw that one out there.

Jacket is another coating not related to insulation. Loomex has 2 insulated conductors, a bare bond wire and all enclosed in a jacket of plastic. Once it was woven cloth.
Some single conductor cables are jacketed and insulated. I have seen these used for street lighting. The jacket permits direct earth burial.