Well if it's any comfort to you, Wiseco has been making piston kits like this one since 1941. The kits for these particular bikes though haven't really been around long enough to have 50,000-100,000 mile longterm tests to determine actual reliability. But Wiseco is an easy company to trust when it comes to big bore kits. They would'nt have lasted 64 years if they weren't. They're definitely a well respected company.
I thought about doing it, but decided against it for now. I'll just wait till it needs it. Hopefully that won't happen for another 60-70,000 miles. Like you, I plan on keeping my bike for a very long time. I think they're going to have to pry it from my cold, dead fingers.

The only additonal recommended mod I've seen for the Wiseco kit is to improve the clutch with a Barnett(another respected company famous for their clutches), or to just put in heavier duty clutch springs.
There's been a couple of dyno runs on Bonnevilles that I know of. One reprot had 75 hp at the rear wheel, but that was with Mikuni carbs installed. Here's an actual dyno run that I got from the New Triumph bonneville forum on Delphi.
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The blue line is a '02 T-100 (reference curve form Dynojet)
= 53.08PS / 55.56Nm at the rear wheel.
The red line is my '03 T-100 before the installation. My setup: TOR's, Dynojet Stage2 Carb Kit (DJ114 main's), Snorkel removed and UNI.
= 52.34PS / 53.89Nm at rw.
As you can see, no remarkable difference (only the sound...)or a weak engine.
The green line is my T-100 after the installation. My setup is the same like above but DJ118 main's.
= 61.61PS / 67.79Nm (at 3300rpm) at the rear wheel.
Now I can feel the difference!
dyno 1 dyno 2This was from a guy out of Switzerland running on a new dyno, so take it for what it's worth.