Lenin? Yeah, he liked to be pictured with kids and cats, all the while he decreed the assassination of thousands. Lenin is regarded "fondly" by those who just remember Stalin all too well. Tito? The guy who was kept happy by his finance ministers not letting the burdgeoning debt and overall bubble of their economy implode before he died, just making everything worse when it did and eventually opening up the country for the bloody revolutions that followed? That guy? The fact that dictators do not usually have worthy "follow ups" is probably because they weren't good leaders from the beggining.
Good dictators don't have worthy follow ups simply because the chance of hitting the jackpot twice in a row is very slim. It's rare to have even one. Also, due to the nature of a dictatorial regime (which frequently masquerades as a democracy), it's very hard to designate a successor and ensure that he actually takes power. Lenin, for example, certainly didn't want Stalin to succeed him, but it kind of "ended up that way" (or rather, Stalin outmaneuvered his opponents and took power for himself, which others didn't see coming). A hereditary system does mitigate that problem, but also limits successors to ruler's own kids, who don't always take after their father.
A good leader doesn't only look out for the country, but creates the means by which it won't fall down when he decides to leave office, etc. And such a system is probably called "democracy". A good democracy not only by name but by process. This idea that what a country sometimes needs is a "Good Dictator" is a very old conservative myth that is so useful for people like Putin and Assad. We should wreck it to bits.
Well, democracy is a system which is incredibly easy to keep relatively stable, but also very vulnerable to crises and prone to giving power to people only good at flapping their gob. Also, it runs the risk of becoming "tyranny of the majority" if the populace is backwards enough. And the sad truth is, stupid people outnumber smart people. An advanced country like Switzerland can run well with it, but it takes a high level of education across the populace. Otherwise you get a situation like in Poland, where politics consists of throwing invectives at each other and trying to blame everything on the opponents, while distracting people with sensationalist news (remember that plane crash which killed a good part of Polish government? Yeah, they're still debating if it was deliberately arranged...). It's probably different in civilized countries, but from my experience, common people are too dumb and too easily manipulated to be allowed to run a country. You just end up with government good at manipulation and not good at any real ruling. And if it's really bad, you end up with things like Sharia law and anti-gay edicts actually enjoying popular support and getting implemented, with the people hurt by them having nothing to say because they're a minority. If the majority is backwards enough to be composed of bigots, then you not only soon get bigoted laws, they're very hard to repeal without changing the general populaces' views first (no small task in most cases).
To then call Putin a "reasonable (if not good) dictator" is, I think, something you don't really want to do. The guy who assassinated reporters who dared speak against him and his cronies? The guy who put his friends into the Oligarchy and let everyone else rot? (Are you even aware of the bleeding nature of the young scholars in that country?) The guy who turns the word "elections" to a running joke in the country, and when someone almost makes history in becoming no 2 with good numbers in an election in the city of Moscow despite all the PR and the media machinery put against him, he's thrown into jail for absolutely ridiculous reasons? The man who is the sole responsible right now for the butchery of Syria, the man who did what he did in Chechnya and Georgia? That man is not a good dictator, not a good ruler at all. Despite oil prices surging msasively in the last 15 years, he has utterly failed to accomplish every single economic objective he had set out to do.
I said he is not a good dictator. I said that he was "reasonable", in that he was not crazy or deluded, like Hitler or Stalin (and indeed, a great deal of others) were. He is a horrible person, but note that everything you mentioned does not, in fact, hurt him. He is absolutely ruthless and rules with an iron fist, letting his oligarchs be the real power in Russia, but still, he made clear that Russia is a force to be reckoned with. In fact, that's the real problem with him. A crazy bigot like Stalin killed off a lot of intelligent people and generally wrecked the country, but Putin actually strengthened Russia a lot. He's very dangerous, because he is both a horrible person and a skilled ruler. And he's clearly not a failure, if he was, he wouldn't be at Europe's doorstep.