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You shouldn't be using anything as rough as a file, you'll certainly never get that back to a good finish. If I'm compounding anything, whether it is gelcoat or clear coat or resin or whatever - if I have to start rougher than 800 grit then I know I'm not going to be able to compound it up to a true full gloss without applying more material to fill the rougher scratches.
Tooling gelcoat is tough and hard wearing and difficult to sand, so you want to be getting your repair job as close to flat as you can without having to do any sanding at all. Sometimes that means doing an initial fill that is a bit low, and allowing that to cure. Then do another smaller fill that just takes you slightly proud of the surface, so that all you need to flat it back is a few minutes with 800 grit paper on a block. If you try to do it all in one application, you will likely get some bits that are high and some bits that are low and it won't work properly.
Another trick I do often for less complex areas is to use flash tape or release film to shape the repair. That works very well for flatter areas and outside radii, but not so well for compound curves or inside radii. You just want to be careful not to wrinkle the tape/release film or trap air bubbles as this will give you even more repair work to do.
As with all hand work - it really just comes down to technique and practise. You won't learn the techniques without trying them, and sometimes you will make things worse. But give it a go and see how you get on. Be patient, don't try to do too much at once. If you need to, multiple fills are often better than one for larger repairs. Take your time sanding, it isn't a 2 minute job.
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