I tend to calculate cpp for airline miles based on flights I take where they're an actual cash replacement. The humble domestic flight (or transborder US/Canada flight) ends up being my baseline. I don't use *most* of my miles this way, but it's the best way to figure out what I should value my miles at when comparing against cash.

In other words, for me, close to 2 cents per mile.

When I redeem international J/F, I just basically think "is this ticket worth more than 2 cents per mile to me?" If we're talking about 120k R/T for a J seat...$2400 R/T for long-haul J...the answer is typically yes and I book it, assuming it never actually sells for below that amount. I don't care what the max-rack rate in Orbitz is, nor what my corporate travel agent would sell it to me for. Unless, of course, they're down in the $2k range for this hypothetical 120k R/T ticket.

I've created wacky F routings for a specific purpose (the LH FCT in FRA being an example) that (rather humorously) priced for $20,000+ in Orbitz. I have my laugh at that, but don't let it cloud my 2-cent valuation for my miles.

For hotels, I usually baseline cpp off of what I'd typically get for redeeming my likely award in a given program. For example, Marriott can be terrible for a 1-night redemption, but the Travel Packages are great. I stay there enough to actually reach the TP levels, so that's how I figure my cpp.

By contrast, I'm a fairly infrequent Hyatt guest, I find their one-night awards to be less of a "penalty", so I just baseline off of a midcategory free night award. Hyatt power-users probably baseline off of something else...I'm sure there are better awards in that program.