since basically you are transmitting across open space (isolation barrier can be an air gap, or apiece of insulating material, same thing electrically), you want to treat this as a radio link.
1 your first drawing is similar to what i suggested but not quite the same
2 the XOR gate inverts the phase of the carrier instead of using on-off keying, and eliminates the DC component (or "keying thump") after passing the signal through a capacitor... the phase inversion rather than on-off keying reduces the signal bandwidth.. a receiver for this signal is more complex, but the on-off keying is more subject to noise and interference from outside sources. the output of the XOR gate is a BPSK modulated radio wave. a receiver using a phase-locked loop will easily recover the original data, and the phase detector of the PLL will ignore most noise as long as the transmitted signal is present.
3 the first design you presented wasn't really differential, and your NOR output signal is on-off keying with differential outputs, and may be suitable for capacitive coupling to an isolated part of the same chip. if however you were looking for this device to have some radio applications, where the receiver is more distant, the XOR modulator with BPSK modulation is probably a more efficient way to get data across a link. the differential output (such as in XOR.JPG) could directly feed a dipole antenna. since the output is a raww digital signal, a lot of filtering would be required between the modulator and the antenna to turn the carrier into a sine wave, but it shouldn't be really complicated. it would be well suited for a HIFER transmitter where low output power and narrow bandwidth are both required. HIFER transmitters operate in the 13.55Mhz ISM band.
4 what you have in post #6, will work through capacitive isolation on the same chip as the receiver no problem.
when i get home from work i think i can clean some of it up and simplify it for you, as well as lay out a schematic of what i had in mind for a radio link (which is what i thought you originally had in mind)...