+xThere's a thread very similar to this one, it might be the one you allude to. Most of the difficulties remain. Although you want to attach the alerts to waypoints, would you imagine the alerts would be saved along with your route, or with your general SkyDemon settings? Again, what happens if the route is changed? What happens if you turn around and approach the waypoint again in the same flight?
I'd imagine the alert would be saved with the route as it's route specific and if the route was changed it would be necessary to move the WP (with the alert) to match the new route (ie if WP was for an RPS boundary or at a 10 nm from destination airfield then if the route was changed these WP's would need to reviewed and changed by the user too.
As for reversing the direction whilst on the route, i'd suggest it would do whatever SD does at the moment if you reverse a route. I've not done it in the air but in simulate mode if you turn around on a route the route directions seem to continue to direct you back to the route. I guess if you formally reverse a route mid flight then that will need to consider if the WP (with alert ) is still relevant for that new route so again for the user to decide.
As it happens I've just set up named WP's on my route to do this for me, so set up WP's named "Call XXX airfield" or "Check RPS" and as that is displayed on my route it seems to do most of what I need.