No, no, no.
The first step is to completely get rid of words "isolated" and "ground", thinking they have some generic value or typical implications. A sentence like "Isolated ground can be connected to ground but it creates a ground loop" is a good example - it's completely void of any meaning whatsoever, and of course, if you try to force any meaning to it, it's just wrong.
Instead, draw an actual circuit diagram of the actual system and look where the currents will flow, based on basic Kirchhoff laws. Draw your "ground" connections and look if you can make your desired currents flow, or if undesired currents will flow.
You can use basic circuit simulators to verify your thoughts.
Isolated simply means there is no electrical connection, and hence no current can flow.
"Ground" simply can mean anything, really. It's an arbitrary convenience "tag" in electronics, similar to a "reference level". Multiple grounds may exist, or may not. Whether they can be connected together is a similar question to whether wires xyz and asdf could or should be connected together. You only know by understanding the circuit.
As for the isolated gate driver, they have the isolation for a reason, and it costs money. You should understand where you are going to connect it and why. Otherwise, you are likely to create high-current short circuits.