I'm sure you'll get some other, more expert, input on this particular topic, but fwiw -
1) No, but for the year & a half I've been running it I don't have that many hours on it. I don't recall that Frank's manual noted any need to check the biasing, though I'll go back and re-read. I think Frank, Dean, Larry, or Wayner should be the experts on that. As to tube replacement, follow recommended procedures, and shouldn't be a problem. I've changed one tube in my T-8, no particular problem. Have the 6CG7 Mazdas on order to start some rolling in the T-8 & Ultra Pre, and am looking forward to checking things out.
2) I'd say 'Yes'. I started with a Halfer to Omega upgrade, then to Insight, and op amp upgrade myself, that was driving the combo 2 channel/HT. I heard a difference with the T-8 pre when I moved the 250 to my office system, and inserted a std Ultra 550. In my case (though not the only 'tube' piece in the chain, Ultra Pre, & Insight DAC) each step up in the AVA lines has provided more detail, more refinement, smoother, quicker response, with a more detailed soundstage. Granted a fair bit depends on the recording, or soundtrack, but I have no doubt you'll hear a difference. Aside, I'm driving std Song Towers with the 550 for the 2 ch & front HT, I'd think you'll be happy using either the 440 or 550 with either the STs or the HT2-TLs.
3) I'd probably say a qualified 'yes', but only when there's no source playing and you have your ear close to the speakers in my system.
Seems to me martyo, and maybe a couple others have experience with the Dbl 550, it's an upgrade that's on my wish list, so they can probably speak to that best. Heat-wise, there's probably a little more with the 550 vs the 250 (260). The combo system is on an open shelf system similar to Frank's, the office with the 250 is in a cabinet. Haven't had any problems in either case.
Bottom line, not that there aren't alternatives as noted my many more knowledgeable than myself, I can't imagine you'd be disappointed in any way. Then again kind of depends on expectations, ymmv.
Office system - Insight '260' with Burr Brown, T-8 pre, Ultra DAC, Dahlquist DCM-7s
2 ch/HT system - FET Valve Ultra 550, Ultra pre, Insight DAC with Burr Brown, Omega 240/3 driving C/LR/RR, std STs, Song Center, & SS Is.