Spraying: clogging and lighting.

I have two somewhat separate questions about spraying interior trim.
I don't normally do new construction, but a while back I did a house where I sprayed all the trim for the first time. I've got another one coming up and wanted to make it a more convenient experience.

I was using (and will likely use again) A cheap Graco airless (borrowed from the homebuilder). Spraying ProClassic through a 310fflp. It kept clogging. Not enough to cause a serious problem, but enough to be an annoying PITA. Do I need finer mesh filters and/or strainers than is normally recommended for waterbased paints? Or does it have something to do with the sprayer itself being a cheap big box store model?

The second inconvenience was the poor ability to see the difference between the wet second coat and the dry first coat. Do I need a much stronger lighting system (was using a couple old 500 watt halogen worklights), shine them at a different angle (tried that, didn't seem to work), or just get used to a "blind" technique of remembering exactly where I've made passes?