I can appreciate the 'clean' results you get, and handholes certainly are expensive (Even a box store version will set you back $30). My way is just the result of too many gnarly repair jobs.
That is, I've had the power run be damaged many times, usually because the feed was simple UF, run just under the sod
. With the small size of most handholes - and many poles lack even small handholes - making splices in the poles can be a challenge. Of course, if there is no 'sweep' going into the pole, there will be no way to re-pull the wires (either because of a sharp bend under the pole, or because of the concrete around the pole).
Often I'll encounter some attempt to use "Bell boxes" for the connections. I don't like the boxes when mounted on the side of the pole, because of support issues, vulnerability to damage, and difficulty in fishing wire. Placing a "Bell box" either in the ground, or in the concrete, is unsuitable for the same reasons, plus the added issues of corrosion, and the fact they fill with water and muck anyway.
Finally, I've encountered several instances of wires either shorting, or actually breaking, inside poles. Without a pull point nearby, you're in for a nasty job.
Between careless drivers, demented gardeners, and simple bad luck, pole lights are one instance where Murphy was an optomist.