A reamp box provides rejection of noise picked up by the cable, and breaks ground loops. Also removes any DC offset from your line out.
With short cabling, good grounds, and an AC-coupled line out these advantages may not be required.
A reamp box also limits bandwidth and adds low-frequency distortion (primarily 3rd harmonic) in the transformer core.
These effects may be inaudible or close-to, but it's difficult to imagine how a signal passed from a DA interface to an amp through a transformer will be more identical to the recorded tone than if the transformer weren't there.
I've reamped from the output of a Delta 66 to a boost pedal using about 5-foot cable, the tone was pretty much the same as plugging the guitar straight into the boost. No noise, no hum.
Straight into the amp should be no different, although I've never dispensed with the pedal. So I can't say from experience.
A 1:1 transformer gave no improvement in noise, and any tonal difference was so subtle I may have been imagining it.
Had there been hum with the unbalanced connection, I would have expected the transformer to get rid of it, but there wasn't.
Bottom line is;
1) long cable runs generally need to be balanced (use a reamp box), short cable runs may be fine unbalanced. Same as any cable carrying low-level signals.
2) If there is mains-frequency hum, break the loop (use a reamp box).
There's too much variation in setups to say whether you need a reamp box. But there's no harm in trying without, and if there's no problem, fine.