Possibly. Russia is more nuanced than we think. There’s a chance Putin will live to old age and die of natural causes. He may want to give up power while he’s still alive and able to have some influence, as a way to measure or ‘trial run’ whoever is replacing him. Putin knows what happened after Stalin, where the all powerful leader died with no clear succession plan in place.
Maybe. The regime hasn't shown much sign of nuance or sophistication, but I suppose it’s possible.
Autocrats like Putin don’t really want designated successors though. Whenever things start going badly, you don’t want your underlings to get it into their heads that maybe it’d be better if General So-and-so were in charge
now. What they prefer to do, and what Putin’s done, is to make your inner circle compete among themselves for influence and the Leader’s favor. So long as they’re scheming against each other, they can’t conspire against you. Hitler and Stalin did the same thing.
What Putin did learn that Stalin did wrong is not to shoot or imprison your generals when they fail. A sufficiently popular general who thinks he’s about to catch a bullet might decide since he’s got nothing to lose, may as well try to take the Big Guy down. Putin’s already had one mutiny. Instead, generals who’ve failed (or been scapegoated) have just been retired or shuffled off to some meaningless do-nothing command. Instead of two in the head or a decade in the gulag, facing a quiet job without much work means they’ll go quietly.
Putin’s way too controlling and paranoid to ever simply hang it up and go home to St Petersburg. His retirement plan, if he has one, is probably not unlike what he did 2008-12, and put a toady like Medvedev in the seat while keeping all actual power for himself. That’s what Qaddafi did - for most of his last 20-ish years in power, he insisted he was retired and only an informal advisor to the head of government. Which of course was bullshit and everyone knew it.