As a member here, I'm obviously a railfan, but I've yet to redeem points for sleeper travel (though I definitely plan to).
I did once redeem points though, 6000 in fact for a pair of NEC One ways (NYP-BAL) last year. Reason being was that my funds were very limited at the time, and my friend and I really wanted to take a daytrip to New York on the train. I coupled this redemption with last years free companion coupon promo, paying $81 and 6000 points for an itinerary that would have costed $352 without either. I could have kept the points and used the coupon for the whole round trip at $176 but money was just that tight.
I just cracked 30K and hope to hold this for a future sleeper trip with companion to get the most out of it, but if the travel bug hits me during tight times, I could very well be left spending points again on less lucrative rewards.
On a similar vein, though a railfan, I could never see myself going to great lengths to book a "loophole" trip where I have to get to a starting point I wouldn't visit anyway and go somehwere I don't care to go. I'm not dissing those who do, but for myself personally, I find it more satisfying to get more out of the trip than just the train ride.
I would however have a problem booking a 2 zone reward that doesn't go two nights. Sort of interesting how it costs more points (20000) to go CHI-BAL 1 overnight on the traditionally cheaper sleepers on the Capitol than it does (15000) to catch the pricier sleepers on the Silver Service, despite a slightly longer ride on the latter.