Glacticosh
I reread your question and to be more precise, you would have to receive clearance for maneuvering airspace above the MSA and be on established on the outbound course before the IAF was passes. How far before? Just enough to be wings level at an appropriate speed for the plane--minimum holding airspace with an additive for 30 degrees of bank should be right.
Ficklefinger
I was answering the original post on PANS-OPS drawn procedures, not TERPS drawn procedures. I'm not running a international procedures class here, but a PANS-OPS course reversal must be entered from within 30 degrees either side of the outbound course and flown as depicted; the US FAA "stay within the airspace, but any holding entry is OK" technique will NOT work. But, as Aterpster has pointed out, there are good reasons to fly the outbound course in TERPS procedures.
At neither of those locations I posted (VOTP and PTRO), there wasn't radar for ATC to see excursions, avoiding mountains was entirely up to the pilots to fly the "black lines".
GF
PS. just to point out, I have been thru the USAF Instrument school and FAA TERPS, it's been awhile, so I could be mistaken in some areas.