Passport stamps

Does anyone have any experience with entering Lesotho (exiting SA) via a border point not housing a border post, and then (2 days later) returning via a controlled border post (Caledonspoort) to exit Lesotho?
Have any issues on your Lesotho exit?
How important is the entry into Lesotho stamp?
I will be honest to them on my route of entry but that area is totally unmanned. Is it known that one may (read as should) not enter Lesotho as such, or is a blind eye given to it as long as you don't do what I'm going to do by exiting the legal way.

I'm running from Sentinel Car Park, along to Namahadi and (this is where the exiting SA/entering Lesotho happens) down to Afriski, staying over the night, then running off to Maliba Lodge in a mostly SW direction the next morning, to get collected at Maliba and then driven out with passport in hand at the border post to overnight in Clarens.

The same problem has been discussed here and here . Mixed responses, some saying authorities are lenient, some saying not. Intrepid said this (2011):

intrepid wrote: They don't like it. Chances are they will let you proceed, but I don't know what would happen if you get an official in a bad mood.

I once had 2 people drop out of a Grand Traverse at Sani. They had their passports but the official was not happy that they didn't have an entry stamp. He gave them an earful and then let them proceed.

We once used Monantsa Pass (which has a SA border post, but no Lesotho counterpart) and took our chances by exiting at Caledonspoort. We we explained we had entered via Monantsa, they sighed and were mildly irritated, told us not to use that way again, and ushered us through without stamping anything in our passports.

It will probably depend on the official's temperament/mood, but it seems you basically have to take a chance if you want to do your planned route.