Well, almost all the problems in my book call for us to get rid of drag as fast as possible. The standard brief before departure is something like:- "Up to acceleration altitude we'll confirm uptrim on the live engine, autofeather on the dead one, otherwise do nothing but sit on our hands, get the gear away and talk about it"
Only three causes I can think of that that would cause us not to retract the gear.
1) Failure of the gear system itself.
2) Wheel/brake overheat and we want to leave it dangling in the breeze to cool it down a little.
3) We forgot (yes, it happens occasionally)
If (3) is the case, we're not exactly going to call you to tell you we're leaving the gear down until we remember to retract it.
In either of the two other cases, you'll hear about it when we're good and ready, if ever.
Sorry to seem dismissive and unsympathetic for your obvious caring about how we're getting on up here - it's appreciated. But the time just after take-off, particularly if we have any problem, is one of very high workload, and I'm not going to promise to call you just to set your mind at rest when we're already working like the proverbial one-armed paper hangar.
If it's any help to you, we don't accelerate beyond V2+5 until 600' AGL. Many companies leave it until 1000' AGL. So you've got all that space anyway, whether we've got a problem or not. The main thing that is likely to change is the rate of climb.
On an ATR, V2+5 is going to be anything from 105-120 kts. Gear limiting speed is around 170 kts. So it ain't gonna slow me down if I can help it at all!