Transmitting is possible, but some of your suggested methods may or may not work as intended.
Combining wired and wireless from the same modulators seems like a recipe for troublesome complications.
I know there are some people who have used a combiner to feed the same modulators to a single antenna, but they usually have to eat 6dB of loss. Finding a distribution amp that can output the 60dBmV necessary for transmitting is difficult.
Most folks who transmit do so with multiple agile modulators and as many antennas as modulators. I've got Ch7 and Ch9 modulators and antennas right next to each other and it's fine...Granted I have the dipoles facing orthogonal directions to minimize coupling between them.
I recommend having the wired and wireless on different channels. On sets with 300 ohm input you'll get multipath from the wired and wireless and that can cause a variety of issues.
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