From what I can see in your last photo, the booster pump is in the right place, however, it will only show the mains pressure on the gauge as the gauge is before your booster pump. It's not a problem because it won't stop the pump doing it's job. You just won't be able to read the pump pressure. To do that you would need to configure your pipework slightly differently. You would need to fit an elbow piece to the back of the canister in your picture and run the pipe into your pump. then between the pump and the RO you would need to fit a 'T' connector, and connect the gauge at that point. Unfortunately the thread size in the canister and the RO are different so you can't swap them over. At least they are on mine.
Beyond that I don't know what to suggest. I think the 300gpd advertised is only achievable in absolutely optimal conditions, whatever they are. I've got a permeate pump attached to mine as well and it just about keeps up with me.