I've made a final decision!
After getting a decision helping e-mail from Frank, it looks like i will do
Vision EC DAC -> T8+ -> Insight Double 260.
The Double 440 really is overkill in my room with my speakers. If I ever do upgrade to ineffecient speakers in the not so near future, I'll probably be ready to change my gear, too.
However, as my grandmother used to say, "Man plans, God laughs."
Thirty minutes after getting Franks e-mail and itching for a break at work so I could order already, my wife called to tell me our house was on fire. Two gutted out bathrooms and a lot of water damage later it looks like I might be out of my house for 90 days. Ugh! Fortunately, nobody was hurt, the fire was contained (and yes, the HT2-TLs are fine), and I'll just have to learn a little patience.