I'm asking similar questions for my wife's bike. Do I upgrade her Giant Innova hybrid, buy a Volpe-level bike or build a LHT?

The problem with the sub-$1000 bike (Bianchi Volpe/Jamis Quest/Fuji Touring/Windsor Tourist/Novara Randonee) is that none of them have the right components. Some get the crankset wrong (road triple), all of them come with brifters (which I don't want), the wheelsets are often sub-par, and some come with wierd seats/seatposts etc. My wife also doesn't want a dropbar or flatbars, so that'll be an upgrade to trekking bars too. At a minimum, this sub-$1000 bike starts to get expensive with the upgrades, or becomes a hassle haggling with my LBS over how much credit to give me for the brifters, etc. I don't want on the bike.

OTOH, I spec'ed out a LHT for her with every component exactly as I want it and it came to just over $1200 with a handbuilt wheelset. That's a much better value than the Volpe IMHO. You just have to avoid "ultimate-itis" on every component. Figure out where you want to spend for top-shelf and where it doesn't matter so much. LX derailers, Sugino cranks and SRAM Cassettes all save money and don't compromise that much on quality. Spend the big bucks on your frame and wheelset.

In the meanwhile, there's nothing wrong with touring on a hardtail mtn bike. You can even make several upgrades to it and eventually switch those components over to a dedicated touring frame when money allows. This is probably the direction I'm going to go for my wife's bike--replace the entire drivetrain on her Innova, change the rapidfires over to barends on Thumbies with mtn brake levers on trekking bars.