Had you lived in Machiavelli's time, would you support his ideas, or condemn them like the pope did?

I would've supported his philosophies. It was crucial in Italy to have unity, even if it meant absolutism. It would've been nice to have a more congenial form of government, but to protect Italy from foreign intervention, any form of a central government would have been good.

If I lived in machiavelli's time I would have liked to have had him around as an advisor but I would not have supported fully implementing his policies. The ends do not justify the means, but sometimes tough action now is better than being injured or destroyed later.

A a strong government does not always make a healthy state and all Machiavelli and no Jefferson/Locke makes a desolate state.

As Eeyore said. Machiavelli would have been invaluable as an advisor to a wise ruler, but a very bad ruler himself. Luckily, an advisor was all he aspired to. I'd say his work was not moral or immoral, but simply political science. That makes him the precursor of today's technical political consultants. But smart as he is about what works politically, would you want Dick Morris leading the country? I don't think so.

IF I lived in Machiavelli's time (circa mid 1400's to 1500's) I would
have gone along with his philosophy. If for no other reason,
because the Pope condemned it.

In Machiavelli's, The Prince, he states that regarding international
relations, rulers should prioritize their state's well-being and disregard
moral and ethical concerns.

A good example of a Machiavellian ruler was Frederick Will (Great Elector).
He centralized Prussia (part of Germany that was the poorest and most
backward), made it a great 2nd rate power in Europe. That was no easy
task!

Napolean was another good example of a Machiavellian ruler, until
he messed it all up. GREED!!

With, "the end justifies the means," I can support it, assuming that you are taking into account his elaborated explanation.

Summed up nicely, the governed can be real jerks. If you're just a goody-goody and never exhibit your authority, then that spells out doom. As soon as the governed get fed up with your rule, they'll revolt, quite possibly killing you and your family in the process.

So, be proactive rather than reactive. Come into their country, and crush them. Ruin their houses, commercial centers, and their economy in general. Make them depend on you for survival, then gradually put the economy back into their hands, making sure that they have trade ties and whatnot.

And who knows...... he might've made a good leader, just not a monarch. As I recall, he held the position of "Secretary of the Ten" the first time that Florence revamped their republic, right before the Spanish put the Medicis back into power.