This is from an anecdote:
Odessa, Privoz. Vendor: - Sour cream, cottage cheese! Sour cream, cottage cheese! Buyer, pointing with a finger: - Tell me, what is this with you? Sour cream or cottage cheese? - Well, this ...
Everything is much simpler than it would seem.
On smartphones keyboards, predictive input (analogue of T9) instead of "so-so" suggests "this to itself". I don’t remember where I saw this myself, I think the last time it was on the iPhone 4S.
So, if I'm not mistaken, since most people are not very worried about how and what they write , for some it is this expression that skips. The interlocutor in the correspondence may assume that this is a familiar speech pattern, which he simply did not know about, and naturally, he can start using it.
I don’t presume to argue, because I could be wrong.
(IMHO) I first heard this phrase from Ruslan Sokolovsky. Before him, in my opinion, no one said that. In his videos, this phrase was constantly heard, so after a while it began to pall. This is noticeable in the example of his "colleagues" bloggers, who also began to use this phrase. For example, Roma Mechanic, Acre and other persons who communicated with him on streams are often worth noticing.
I think that Ruslan himself took this phrase from someone and started to force it. But from whom I do not know. (Although it can be assumed that he himself created it by reducing the phrases: "Well, such a thing / Well, such a thing / Well, so-so.) But I think that the popularity of this phrase came from him.
Well, and how it is used by all and sundry seems to be clear. (Ruslana aka Trainer of Pokémon of All Russia Sokolovsky).
But in general, well, that.
The expression "well, this" is typical for the speech of poorly educated people who do not have enough words for an accurate, clear, vivid expression of their thoughts. It is difficult for them to find adjectives, phrases to describe objects, phenomena, events, so they use the parasitic expression “well, this”.