We just picked up a 19' Funlite yesterday and we have 2 tow vehicles - a Honda Ridgeline and a Ford Expedition.

On the Ridgeline (haven't tried the Ford yet but its higher) - the rig sits pretty low, and I scraped the jack stand a few times while coming in and out of parking lots.

If I flip the trailer ball I will nearly level out the trailer and probably avoid this altogether. Is that safe or a bad idea? I feel like I've read that you're not supposed to do that but can't recall.

You can flip the stinger as long as the ball shank is the straight type and not the tapered type. On some balls and stingers, the hitch ball has a straight threaded shaft to tighten the ball down with that then tapers wider and it fits into a corresponding tapered hole in the stinger. If the hitch ball shaft is straight all the way up, then you can flip the stinger with no issues.