Unless you're going for something experimental and want to spend a great deal of time on it, waypoints have been long proven to work beautifully. Generating them in realtime is a bad idea. If you don't want to place them manually, then you'd write a program to generate them and ship them out precompiled alongside with the map.
I have no clue what you mean by dynamic mapping.
Everything you said is obviously possible, it's just the amount of skill you have and the amount of time you wish to devote to it, but take into consideration about how practical it is.