What kind of wire?
If it's a power wire, why is the place wired with conduit?
Commercial buildings must put all power wiring in conduit, so if you're planning to run romex in a commercial building, the answer would be "no", it's not permissible.
If it's data wire, note that there may be some "crossover" interference if the data wire follows a power wire for very much distance. It's usually not a problem to cross a conduit and tie to it, but it's generally recommended that you not tie data cable to conduit.
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Yes. If they are single wires they need to be in a conduit.
No, the bare copper grounding conductor can not be in a conduit with other conductors. It can be in conduit by itself to provide mechanical protection for the wire.
A 100 foot fish tape and wire lubrication will be needed to make this wire pull.
You can pull 10 #3 gauge wires in a 2 1/2" conduit.
No, the electrical code requires that the mineral insulated cable be strapped at proper intervals and not be piggy backed on to other conduit structures.