Russia’s delivery of Yakhont missiles to Syria represents the fulfillment of earlier contract obligations but with updated guidance technology. 
In 2011, Israel Matzav noted of the Yakhont:
“Israel is the only one in the region the Yakhonts would be used against. However, because Iran is supplying (unofficially) the cash for the missiles, there is also the risk that some of the Yakhonts would end up in Iran for use against numerous targets in the Persian Gulf.” 
Add to that risk: Israel Matzav notes the new missile as having twice the speed of the old one (and, again, improved guidance).
How far does President Putin wish to go with supporting, essentially, Brigadier General Maher al-Assad?
I may not be paid enough (nothing, actually) to answer that question.
Above: March 16, 2013 – Anti-Assad protesters walk toward 10 Downing Street, London.
YouTube poster of the video “Thepeopleofsyria” notes, “What a shame, the world and the Media are busy with the length of the beards of the demonstrators in Syria, while they are forgetting about the length of the scud missiles of Bashar, which are coming down on the heads of women and children.”
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I’ll take a little turn here — first confessing that I really don’t know how to answer the question I posed, which has two parts: 1) the fundamental psychology in personality supporting attitudes toward others; 2) dependent and co-dependent interpersonal relationships with significant others and closely associated constellations.
What is most known is Moscow’s antipathy toward “political Islam”, the continuing simmer of restive states-of-affairs in Chechnya, and Putin’s own desire to encourage what psychologists call “narcissistic supply”: i.e., he really doesn’t want to be “the bad guy” — consequently: he really isn’t.
Putin himself would not fire a weapon at mere passersby on a street corner.
Bad form, bad style, all of that.
Moreover, Putin seems to me to have his “back stage” and “front stage” self-presentation in better order, and he seems also to know limits, moderation, and restraint. After all, he works with a whole Russian People.
His associate may not have access to that grace that is the expression of a different mirrored self.
It’s hard to tell.
In 2012, writing for The New York Times, journalist Anne Barnard punched this in toward the end of her analysis of the Assad family’s position:
“The Assads were raised by their father and their uncles — aggressive men — to believe “they were demigods and Syria was their playground,” said Rana Kabbani, the daughter of a prominent diplomat who knew them growing up.” 
In the west, people prefer to see their demigods with guitars, not armies, and they much prefer to hear them singing then to watch them writing laws for everyone else to follow.
In any case, it is not good to have too much power, which is corrupting, much less to exceed limits with it, which is damning.
Analysts in Russia, one of Syria’s staunchest allies, say that as rebels try to encircle Damascus and cut off escape routes to the coast, the mood in the palace is one of panic, evinced by the erratic use of weapons: Scud missiles better used against an army than an insurgency, naval mines dropped from the air instead of laid at sea.
The expected arrival of the P800 Yakhont supersonic anti-ship missile in Syria is considered the first serious attempt by Syria to directly challenge the Israel Navy since the 1973 war, when the Israeli Navy sunk five Syrian vessels in the first missile-boat engagement known as the ‘Battle of Latakia’.
December 2, 2011: Russia has supplied two Bastion coastal missile systems to Syria, concluding a controversial $300 million arms deal inked with the Syrian government four years ago.
House of Mirrors. “Malignant Narcissist, Covetous Sociopath, Bully, Liar, Slanderer . . .” May 28, 2011: “For the narcissist believes that everything belongs to her, and if someone has a little of it, then she’s not getting all of it. Pathological greed, entitlement, and covetousness are what makes the malignant narcissist a dangerous predator.”
Khalaf, Roula. “Bashar al-Assad: behind the mask.” FT Magazine, June 15, 2012. Lead: “They burn his effigy in towns drenched in blood by his security forces.” Of the patchwork of stories I’ve thrown into this section, this piece, which is coming up on its one-year anniversary, may be the one most rich for insight into the political, psychological, and social workings of the Assad regime.