Ok - I'll take the bait
(1) You could give a VMC-only aircraft (or non IMC/IR rated pilot) a steer that takes it right through a bank of cloud, which is likely to be invisible to you on radar.
Wouldn't happen. The only aircraft that get 'steers' (as in assigned a heading) are IFR on a RAS or aircraft on a RIS being vectored for an instrument approach.
(2) You could ask a Piper Cub to take a route over a town that complies with the 1500ft rule, but not be aware that, unlike the last one you handled, which was on a CofA, that particular cub is on a permit and therefore not permitted to overfly built up areas under any circumstances.
Again, wouldn't happen. He'd be asked to route to one side of a point (north/south/east or west) for traffic reasons - how he did it would be up to him to enable him to operate iaw the regs.
(3) You could clear a Shadow onto finals at Shoreham on runway 25. But, because this is a microlight Shadow, not a group A Streak shadow, it isn't (until the rules change later this year) permitted to overfly the adjoining conurbation even on finals to a licensed aerodrome.
Ok, you've got me there, but I don't work at Shoreham

I would say however that this would fall into the "discuss and you'll get what you want category" rather than a more obnoxious "I'm not doing that, because it doesn't suit!" category.
So - 1 out of 3
All of which would be instructions given by you in good faith and applying your best level of professionalism, but where the pilot if he is doing the same would be REQUIRED to decline the instruction and ask for an alternative.
Which I sincerely hope he/she would do
(Quick example: Transitting a lump of class 'D' a few years back en-rte to my home airfield, operating a Seneca, showers and cloud going through the area. ATCO says "Cleared to transit maintain 3000ft, Remain VFR". My retort was "You get one or the other, you don't get both

)
CM