I have not decided on UHF/UHF or UHF/VHF, that is why I ask about both. I gather it is easier to isolate if UHF/VHF?
Yes, isolation becomes easier as the frequencies become further apart. Running a separate UHF and VHF transmitter with a diplexer is no big deal. Running duplex with two repeaters that have the potential to be transmitting at the same time IS a big deal.
However I am partial to UHF/UHF. I assume all this would need to be tuned by a technician at the site location to be efficient and effective?
A technician could theoretically put it together and tune it on the bench, and then have it installed elsewhere. But to really optimize it, it's best to be on site with the right instrumentation and know-how.
May be a good time to refresh on using an Oscilloscope.
An oscilloscope isn't going to help you here.
You're going to need either a network analyzer, or a spectrum analyzer with a tracking generator for tuning the duplexers and cavities. You'll need a service monitor, you'll need that spectrum analyzer for verifying that your combined transmitters aren't creating any mixes (intermod), you'll need an iso-tee, some 50 ohm attenuators, a watt meter, and a directional coupler.
You'll also need to be well versed with a Smith chart for calculating the critical length cables that will be needed. The network analyzer will be perfect for measuring things, but lacking that, one of the MFJ antenna analyzers will do to get you the data needed to plug into the smith chart.
As you can probably see, doing what you want to do is quite possible, and it can be made to work quite well. But it's pretty involved, especially without the background and the tools.
You might be better off with separate antennas. It'll certainly be cheaper.