First off, welcome to the12volt.com forums. Second off, the only dumb questions here are the ones you don't ask. There are lots of new people and people who are afraid to post. So you're not the only new person to installations so don't feel dumb about this, ok? >^.^< "meow"
That said back to business. You'll have a couple of options here. My recommended way of getting that glassed look to it would be to get a high-build primer/sealer for the enclosure. They come in spray cans (easiest to work with) and in paint cans (little bit cheaper but I don't buy these... too much work sometimes) for about $10 can at most art stores. Build up several medium-light coats on your enclosure (usually 3-5 coats if you are going to simulate FG) Then hit that with 400 grit sandpaper to even that all out and get rid of the "orange peel" from spraying. Then use 600 grit to even out the 400 grit. Spray your paint on and clear coat on that. This is assuming you are using spray cans and don't have an HVLP paint gun available.
A note/warning about spray paints (after the primer sealer) It is stressed that you get paints that come from the same brand and series of paint for your projects. Using different brands, and in some cases even different series from the same brand, will often chemically react to each other and create "tears" in the top layer of paint. If you must use different brands/series of paints (say color availability is limited) wait for the lower layer to fully cure before adding another layer of color)
If you really want to go nice on the color, here is something I did in school one time and the teacher loved the work. He said it look truly professional. After your get your colors on and ready for clear coating. Get several light layers (and I mean several) of clear on... Take your time. Rushing will screw this up. Once you have several layers of clear coat on (I like a dozen or more at least... yes it seems excessive but trust me on this one) and that is fully cured and dried, wet sand the project with 1200 grit sandpaper to polish the project up. Hit it with a automotive liquid wax (meguire's for example) and that will get you a FGed automotive finish that will look spectacular.
For your suggestion: You can use resin on the outside, but in all honesty, doing the prescribed method above will give just as good a finish and not give any potential ripples or slight waves you'll often see in flat FG runs. You won't need to lay mat down either. Just sand off the wax that comes up when resin cures (60-80 grit works great here) an then lay filler/bondo to that and get it to the painting stage.
A tip for either way you go about doing this project. Take your subs out of the box and apply a layer of carpenter's glue to the inside surface of the box. It will shrink slightly as it cures and seal the box better for one, and two it will help reduce the pressure through the wood (assuming it is MDF) and into your paint, making the finish last longer.
Ganbatte ne!
Never send your ducks to eagle school.
The difference between ordinary and extraordinary is that little extra.
The 3Ls of life: Learn from the Past, Live for the Present, Look to the Future.