Since division of assets are being discussed, I have read up a bit on independence negotiations and how they would have gone. They actually go for any future negotiations.
First things first, there would have to have been a division of assets. There are a list of fixed assets which wouldn't be under debate. Buckingham Palace wouldn't end up controlled by the Scottish State and Edinburgh Castle wouldn't be under the control of the UK. These would be relatively straight forward.
But if you dive into this further, there would be questions. Embassies would, I assume come under the control of the UK, but this being the case there would have to be a payment to any Scottish government for loss of fixed assets. This would be an area of negotiation.
In terms of milirary, although the number of Scots in the UK military is over-represented (8.6% of the population, 10% of the military), the number of bases actually located in Scotland is less than average. And this raises the question of Faslane. Again, what would happen to the Nuclear Submarines is important. The Scottish regiments would be straight forward. The personnel in other areas not so much. I can't see a prospective Scottish Defence Force being that large so this should, Faslane aside be relatively straight forward.
North Sea Oil is also an area where there would be debate. Would the maritime border be the one historically agreed or the one signed into law when devolution was rolled out in the 90s? This is the difference between Scotland getting around 86% of the oil and gas and 96%. It is a major area of debate. I can see a trade of happening here between the border and debt.
The Bank of England is also a major asset of the state. Would Scotland get a share of the Gold Reserves. Would currency come into the negotiations? This could be a real sticking point. Based on the Velvet Divorce, I could easily see a flight of Capital from Edinburgh to London if a currency union was established. Jim Sillars was probably right in saying you would likely end up with the return of the Pound Scots within short order pegged to Sterling.
Then Pensions come into the equation. like the Bank of England, this could be a real sticking point. The UK would have to make some sort of agreement on pensions, but I could easily see Scotland ending up worse off albeit with an agreement in place. Pensioners would end up with pensions, but less than they are getting at present.
Would debt be calculated on terms fo population, GDP or even by calculating what the debt was spent on? Note that this goes down to the level of spending on the 2008 crash. If this is the case, Scotland wouldn't be as badly off as people think. Although both HBoS and RBS were registered in Scotland, most of the debt was accumulated outside Scotland so it would minimise the actual debt that lands under the Scottish government.
Of course, the Irish Free State scenario could occur where no variable assets are handed over but the Scottish state starts off debt-free. I can't see this happening though.
This leads onto the land border. Ironically, in 2014, this would likely have been one of the easiest issues. Although Scotland would be out the EU, EEA membership would have been a stick on and it would likely have remained open until such time as a Brexit vote happened. If it happened given there would be no guarantee a government which lost Scotland would have won the next election. This is actually one of the biggest changes between now and then.
There would, however be supply chain issues as internal regulations change. This is a major reason why Scotland would be worse off for a period after Independence as companies which covered the British market would change their model to the two states.
Independence would have happened in 2016 but negotiations over the minutia would have been going on for over a decade after, again as with the Velvet Divorce.
During this time there would be a lot of chaos and uncertainty. It is a major reason I voted no. It would have worked. Whether it would have been better or not is debatable.
Most likely not, barring some major change.