"By going with the Denon now, I will be fronting the cost of the Denon ($1000), a new receiver with the new decoders ($1200 est), and an amp ($1500-donâ€™t know if I can score the same deal later) in the span of 24 months. That is $3700 bucks.
If I go with the 755 & Pio VSX 1014 mix now, I will be paying $1200 now and $1200 later on a new receiver. That is $2400 compared to $3700. I will save $1300 bucks. "
Sounds to me as though you answered your own question right at the top of the thread with this reasoning. And I definately agree with that reasoning. Although I've never heard either the 3805 or the Outlaw/Pioneer combo, I have used a similar combination for some years: an older Yamaha 795a receiver (circa 1999; DD, DTS) with a Parasound 1205a amp (140x5wpc). Was tremendously satisfying. But after some time, I naturally came to desire the features of the newer receivers/pre-pros available, and since the price of a dedicated pre-pro is far beyond the wallet of a mere peon such as I, I demoted the 795a to another room of the house, and replaced it with a new Yamaha 1500 (serving as pre-pro only) in the main HT room, retaining the Parasound amp as the balls of the outfit (coupled with an additional two-channel Parasound amp for 7.1). In a couple years, once the fire-wire, HDMI, DVI, I-Link, Blu-Ray, HD-DVD nonsense is sorted out, I'll swap out the receiver again for a more more current model, and retain the amp(s), assuming fitness. My point is that features of the processing department are constantly improved, but power never goes out of style.
If you're only planning on using your current speakers for another year, with a greater pair on the horizon, my suggestion is that you bite the bullet for the twelve months, and eventually swap out the Outlaw pre-pro for something more current (even if it winds up being a an un-amped receiver) in the future.
Quick summary of this long-winded post: if it was my money, I would not consider the Denon for a second (and I've no axe to grind with them). Repeated caveat: I've heard neither of these set-ups in action.
Best of luck, and cheers.