I like the way I can fly S/E NVFR using NDBs, and M/E IFR Using just about everything (Still working on my TACAN and radar approaches) and but cant fly M/E NVFR at all. Seems like the regs have gaping holes in them that don't cover everything.
If you can prove that you have passed an en-route obstacle then you can re calculate your lowest safe and descend to it. That being said you would want to be REALLY sure you had passed the obstacle before re calculating. How you do that can only be based on the items you are endorsed on NDB, RNAV, VOR.
Some nights you can visually identify your location fairly easily as all the distracting ground clutter is missing and only the prominent features remain, other nights you will feel like you are flying into a goldfish bowl painted black on the inside with nothing but the glow from the AH for company
, on those nights I strongly recommend hanging around at 8500ft and descending over the top of the airfield