What size are the tires on the Roadini? I seem to recall reading that that frame can take 42s?
I don't ride fast singletrack, with the exception of a few bosque trails that are narrow due to vegetation, but they're flat; also sandy -- the sand is why I had the #1 Matthews built, to get a more or less road position, gearing, and feel with 60 mm 700C tires for the sand. And I very recently put a drop bar (Spec Hover) on the Monocog which makes it very much more pleasant to ride, but that has 3" tires.
When I took my '99 gofast fixed gear onto ditchbank roads a couple of months ago with 42s (labeled) 39s (actual) in place of the 28s, it was really fun, only that sort of tire is very limited because of our sand; works fine in cold and wetter weather, but 3 hours of sun and heat and the sand gets 2", 3", 4" deep -- no good. Even in March, still sub-freezing at night, it was touchy in places, and I was using the direct/76" and low/57" SA TF hub so I could power through the sandy bits. But the bike was so nimble and flickable compared even to the #1 Matthews, which rides nicely, and while both have drop bars, the lower bar position on the '99 did add to the agile feeling, I expect. Of course, the Matthews is 32 lb with frame bag and contents but no bottles or other luggage, while the '99 with the TF weighed 18.7 lb (18 lb even with Phil and Dingle).
But I'm tempted to build up that '70s Libertas racing frame with (true) 38s and road components and a fixed gear or at least a ss drivetrain; we'll see.
If I rode firm dirt trails, my Matthews #1 would get 44s right away; I'm still thinking of swapping the Big Ones for Snoqualmie Passes.
My last 26er conversion had drop bars and 60 mm tires and a single 64" (IIRC) fixed gear; lovely bike for pavement/sandy bosque trail transitions. I've drop-barr'd other MTBs but those were mostly ridden for commuting on pavement.
Funny: I recall trying my (drop bar'd) 1992 XO-1 off road, and finding it very unpleasant; the front end was somehow just too squirrely in even shallow sand. The later 1999 and 2003 26" wheel road customs were just as agile, more serene on pavement in the transition between straight and corner, and less nervous-making in shallow sand -- all of which supports my long-held opinion that the XO-1 was an immature design immensely surpassed by such road bikes as my 3 26" wheel customs, on one hand, and the original Atlantis on the other.