/u/zamieo

Great question. I will start by giving some background to the situation in 1514, both local to the Low Countries and more broadly in Europe, as you know very well this is the crucial first step to Charles V's reign as emperor and ruler of a large collection of domains.

The TL;DR is this. Yes, significant revenues were gained by Maximilian, but there were important political considerations such that the Netherlandish entities wanted to have a local lord, not a distant lord that Maximilian was to be.

The Low Countries come under Habsburg rule

The Low Countries came under the Habsburgs through Maximilian's marriage to Mary of Burgundy following the demise of Mary's father in 1477. As she faced an aggressive France on her own, Mary had to make significant concessions in 1477 and had to agree to Great Privileges. These privileges include the estates-general consent before any war or tax could be declared, and for the duchess to marry. When Mary herself died in 1482, her will stated that Maximilian was to become regent on behalf of the true heir Philip the Fair, who was born in 1478 and was literally an infant when Mary died.

Maximilian's attempt -- at this time not yet Emperor of the HRE -- at becoming regent over the Low Countries was not straightforward, as the estates-general wanted to protect their Great Privileges. This was greatly incompatible with Maximilian's imperial ambition. Further, France desired areas west of the Scheldt, so the French actively supported revolts against Maximilian's regency. An example of this is the series of revolts in Flanders and Brabant in the 1480-1490s period. The Low Countries entities were worried that they would become a periphery from which income was gained but little-to-know benefits were conferred, for example with the expected requirements to contribute to Maximilian's election when his father was to pass away.

Further they had strong trading ties with France that would be threatened when conflict between Maximilian and France were to break open. The one lucky thing for Maximilian is that Flanders and Brabant themselves competed with each other (and with every other entity in the Netherlands ..... ) so he was able to concentrate the suppression of one or the other. Things came to a head in the late 1480s as Maximilian went to war against France and wanted money from the Low Countries, with a wide range of rebellion from Flanders, Brabant, all the way up to Holland and even in Guelders. It took until the 1490s for Maximilian to take sufficient control that he could wage war against France and have control of his inherited territories over which he was theoretically regent.

Over that period, rebel leaders claimed that their true loyalty was to Philip, with the hope that Philip would be easier to manipulate at that stage of his life -- literally a child! Of course, that was strictly a short-term hope, as Philip came of age, took his inheritance and started a campaign to restore royal control over the domain. For example, he re-founded the Great Council in Mechelen, which was disbanded in 1477 as part of Mary of Burgundy's compromise. And of course, when Isabella died, Philip hurried to Castile to claim his inheritance there, through his marriage to Juana the Mad.

Charles as heir to the Low Countries

When Philip died in 1506, Maximilian once again became regent, however at this point he realized he needed a representative in the Netherlands. So he appointed his daughter Margaret of Austria to become guardian of Charles and governor-general on his behalf. The same political concerns flared up again. But what was special about 1514?

Since the start of her governance, Margaret had encouraged closer ties between the Netherlands and England, and a strong stance against France. The former was to be fully consummated as Catherine of Aragon was married to Henry VIII and then Charles was to be married to Mary Tudor. Margaret herself was a very able governor-general, with great results everywhere including Burgundy itself. The outcome of this was greater trade and economic ties between the Netherlands and England -- and dependence on each other.

However, Maximilian and Ferdinand of Aragon disagreed on the plan to marry Charles to Mary Tudor, and thus that marriage was never made. The result being, a disappointed Henry VIII aligned himself with France against the Habsburgs. This all resulted in decline in Margaret's reputation and credibility relative to the estates-general. One key actor in all this was William de Croÿ, Lord of Chièvres, a Netherlandish nobleman and tutor to Charles V. He maneuvered so that the estates-general of the Netherlandish territories demanded that the Emperor declare Charles to be of age, with the implication that he would take control away from Margaret and Maximilian, and hopefully under the influence of Chièvres.

Thus, the estates-general offered Maximilian a compensation of 100,000 guelders, bypassing Margaret completely. Negotiations went back and forth without Margaret in communication, finally settling at 150,000 guelders. We may not know exactly why Maximilian did this, but in that period a rising Francis I started to enforce his ambition in Italy and in particular in Milan, which Maximilian saw as key to security in Italy, both for the HRE and for his own imperial ambition -- all his life he could not reach Rome for coronation by the Pope despite his best efforts.

Margaret was clearly disappointed and admitted to depression, but Chièvres turned around and tried to win her allegiance to Charles nonetheless. Both saw her talents and that they need her help in both centralizing the Netherlands and also to steer a safe course surrounded by great powers.

As Maximilian died and Charles started to pursue the HRE Imperial title for himself, he brought Chièvres in his entourage and asked Margaret to once again be governor-general and regent of the Low Countries on his behalf. Thus, Margaret had two distinct periods of governorship in the Netherlands.

References

Want to know more? OOoof ... (in the style of a Flemish woof-shrug), you'd have to read a few books. But the greatest detail is in Jane de Longh's Margaret of Austria, Regent of the Netherlands, published in 1953 during the golden era of english-language books on the early modern era. More details on Maximilian's situation can be read from either Wilson's The Heart of Europe or Whaley's Germany and the Holy Roman Empire. Some detail can be read from Maltby's oldie but goodie The Reign of Charles V.

Unsurprisingly, books on Charles V tends to focus on his imperial greatness, not so much on the challenges of ruling his empire. That's why I love Tracy's book and I hope you enjoy it, too.