I've noticed sometimes when creating maps that once on the road the Harley system has me exit hwy and then get right back on... What a hassle. Has this happened to anyone else. Fix?

 

You need to check your NAV settings, and adjust to give you the results your after.

Example:
Your custom map you created leads you along a scenic road from point A to point B.
But there might be an interstate highway between the same two places, with on/off ramps to along the way to that same scenic highway.

Your NAV unit is set to "fastest" route.

So, the NAV will continue to try getting you on the highway to follow that fastest route.
And if you have a few waypoints on that scenic route, the NAV unit will direct you off the interstate and back onto the scenic route to hit that waypoint.

Fix:
Put in a few (or more) waypoints along your preferred route, to keep the NAV unit from directing you onto the interstate.
Or adjust your NAV settings to avoid highways.

Note: All GPS units work like this, so this isn't just an HD Boom thing.