Some AFMs or related operational documents will give you data for the consideration.
However, one needs to keep in mind that, if you do your own thing .. you may be called to justify it subsequent to a mishap or other conflict.
Doing the occasional non-standard operation with requirements to do further actions in the event of this and that .. might be setting yourself up for a surprise. I'm sure most of us can recall the odd time the gear has been overlooked for whatever reason and not picked up until after takeoff scan time .. ?
Generally only a concern if you are using very heavy braking .. eg accel stop testing or similar .. when leaving the gear down is the technique used to manage the heat buildup problem.
Another approach is to retract the gear, get a suitable amount of air underneath you and then extend it to address your concerns without terrain worries.