Bill...Take off the skidplate. Nothing collects in the bellhousing because anything thrown up by the front wheel hits the radiator and oil pan. If anything does collect in it which I have not seen, simply hose it out..no problem. I happen to have an alternator cover which also shields the pulleys and takes a lot of the spinoff. The trans cooler is also unobstructed without the plate and I also don't mind more air flow going into the bellhousing to help cool the converter and trans.
I have 12,000 high speed miles on the bike since the skidplate removal and have had no problems at all. Remember the bellhousing is just an open area in which the sealed converter lives and has no mechanical function. My tranny cooler lines are hanging in the breeze hitting nothing, Used a hanger strap on each of them by drilling and tapping the edge of the bellhousing with 1/4-20 allens to secure them.. If you need the plate for protection you are in trouble already because you will have bashed the pipes and probably cracked the bellhousing anyway. Are you using the Boss off road? I somehow doubt it!
I'll bet most here have removed it because it is just a pain in the ass for all kinds of things including trans fluid changes. Just use it as garage art as I do. The tranny cooler has no dings but you will have to clean it with your hose when you wash the bike which just tells you it is in the air flow where it belongs. The factory stacked model is quite strong and rigid.
If you must have the skidplate (and I don't know why) move it down to "unsandwich" the cooler lines and allow them to just lay on the skidplate. You'll have to slot the front mounting holes in the plate to allow you to do this. Don't bother and just remove it....Joe