The chances of this happening were very slim.
The Acts of Union, signed in 1707, was incredibly unpopular in Scotland, unrest broke out because of it. However, this did not translate into popularity for the Stuarts, who were associated with Catholicism and the oppression of the Kirk (who, despite their fairly brutal methods, revolutionised education in Scotland; especially Lowland Scotland). It is also true that a majority of clans (mostly Catholic) also did not rally around Charles. Some were even pro-Hanoverian. As such, the Stuarts did simply not have the majority of Scots on their side.
The plans for the French to reinforce Jacobite soldiers collapsed in 1744 before the rebellion, and support like this would have gone a long way in improving the chances of effectiveness. The army was tiny and he lacked the finances and arms to mount a serious challenge to George II.
In the initial weeks and months, the Jacobites were stunningly effective but because of failures of the Hanoverians rather than any real strategic success of the Jacobites, i.e. troops being deployed elsewhere abroad to fight the regime's wars abroad with only a few left to defend Scotland and the reluctance of the Lowlands to die for George II allowed Charles to sweep through large parts of Scotland, eventually occupying Edinburgh. Success continued at the Battle of Prestonpans where the Jacobites routed the government in "less than 15 minutes".
The Battle of Prestonpans effectively meant all of Scotland was under Jacobite control. With such domination, Charles marched into England, a move which began the uprising's undoing. Had Charles halted his advance to Scotland, it is likely that George II would have been brought to the negotiating table, but instead, he wanted to take England and persuaded his council to vote in favour of further military action by one vote, with the promise of English Jacobites and French military assistance.
As they marched southwards, few of the promised English jacobites enlisted, with the greatest support in Manchester - 400 mostly Catholic men. Charles had made no attempt to approach Jacobite sympathisers, but even then, such sympathisers (what little of them that existed) had never truly indicated that they were willing to take up arms against the government.
The leader of the Jacobites' left-wing and effectively Commander-in-Chief Lord George Murray had lead and won Prestonpans on his own initiative, and from then, a chasm began to form where Charles and Murray began to disagree over military affairs. Murray opposed Murray's plans to march southwards and advised against them. Nevertheless, Murray followed Charles orders and invaded England, conducting the successful Siege of Carlisle. However, when the town surrendered, Murray relinquished command on the basis that Charles was actively undermining him. Murray's replacement was disliked by the army, and so Charles quickly reinstated Murray and marched towards Derby.
The Jacobites had managed to reach Derby, in the East Midlands of England. This is where Charles' empty promise of English Jacobites joining in support had begun to catch up with him and the cause. Three armies were against him now - one lead by Wade in Yorkshire so posing minimal threat, one lead by the Duke of Cumberland and another in Finchley, north of London to defend the capital, as the elites there had begun to grow uneasy. Charles wanted to go on yet further but Murray urged him to retreat, citing this lack of extra support as something which would threaten future success. Having support of the council, Murray managed to convince them to agree to retreat and Charles, furious, sidelined Murray, who was relegated to leading the rear-guard.
In the final days of the rebellion, the Jacobites on two occasions decided against ambushing the government, and consequently, they missed the opportunity turn the war back in their favour. The Government was defeated by the retreating Jacobite army in Falkirk, however Charles chose not to exploit this victory and continued to retreat, towards Inverness. Cumberland's men followed. Cumberland's army were forded at the River Spey in the Highlands. On this occasion, the Jacobites occupied high ground overlooking the army, but were ordered to withdraw.
The Jacobites had their last stand at the Battle of Culloden on April 17, 1746. Cumberland set up camp in moorland near Culloden. Charles had formed an army of Jacobites a mile away. The weather was unfavourable, with rain and sleet blowing in the direction of the Jacobites and open moorland site, chosen by Charles against the advice of Lord Murray who postulated that the open moorland benefited the Duke of Cumberland's artillery. Cumberland's troops blew gaping holes in Jacobite ranks, as orders were awaited. When the order was eventually given for them to charge, few Jacobites reached the government's lines.
After this defeat, Murray tried to organise continued resistance but was eventually dismissed by Charles, who by that point had fled to Skye. Cumberland's men advanced - Lieutenant General Henry Rawley would report that the government's army "cleared all the country for three miles before them and...made great slaughter every way" and consolidated the Highlands under their control through brutal means like cultural cleansing and precipitated future anguish in the Highlands which would last for generations, the effects of which are still clear today.
TL;DR:
the majority of Scots opposed the return of the Stuarts to the throne.
Lord George Murray was always somewhat more competent and was always ignored, and eventually completely sidelined, by Charles. His aide-de-camp, James de Johnstone, wrote: "had Prince Charles slept during the whole of the expedition, and allowed Lord George Murray to act for him according to his own judgment, he would have found the crown of Great Britain on his head when he awoke."
Charles was a gambler, and too often his gambles did not pay off.
He could not inspire support in England, leading a largely feudal army into an emerging capitalist state.
When the Jacobites eventually came up against seriously skilled troops (Culloden), they did not stand a chance
Sources:
People's History of Scotland, by Chris Bambery, 2014 (Verso)
The Battle of Prestonpans Heritage Trust
[BBC - History - British History in depth: The Jacobite Cause] (http://www.bbc.co.uk/history/british/civil_war_revolution/scotland_jacobites_01.shtml#three)