You wouldn't know it if you weren't paying close attention, but we have entered the largest military escalation since Obama's failed Afghan 'surge' in 2009-2010.
There are three critical differences between that surge and this one:

1) there's been practically a voluntary news media blackout about the current escalation
2) this escalation involves more than one country
3) the current escalation is constitutionally questionable

Let's look at the scale of the escalation.

Iraq

“The boots on the ground have to be Iraqi.”
- President Obama, September 2014 interview

There are 3,650 U.S. troops in Iraq at present, part of a 6,500 man coalition, and the Pentagon says we must send more.

"Boots on the ground? We have 3,500 boots on the ground" in Iraq and "we're looking for opportunities to do more," Carter told CNN's Fareed Zakaria in an interview last week at the World Economic Forum in Davos, Switzerland.

Make no mistake, these are combat troops.
In reality, the number of Americans in the Iraq war is closer to 6,000, plus another 800 soldiers have been requested.
In June 2014 there were only a few hundred American soldiers there. Recall that when the war started Obama promised us “limited,” “humanitarian” airstrikes. That's a far cry from the situation today.

“As commander in chief, I will not allow the United States to be dragged into another war in Iraq,” said Mr. Obama, who built his run for the White House in part around his opposition to the war in Iraq.

It seems ironic that votes on the 2003 invasion of Iraq is part of the political discussion today, but a military buildup that is currently happening is mostly ignored.
Also unexamined by the news media and public, is the increasingly precarious economic situation in Iraq, where the government is going bankrupt at an alarming rate.

Ali Khedery, the CEO of Dubai-based Dragoman Partners, a former adviser to US Central Command, and a former Exxon executive with extensive on-the-ground experience in Iraq, warned that cheap oil threatens the country's last remaining semblance of order.
"You are looking at a significant possibility of state collapse due to civil unrest," he told Business Insider.

I don't believe our political or military strategy accounts for an outright collapse of the Baghdad government.

Syria

16 times President Obama promised there would be no boots on the ground in Syria.
Late last year, 50 special forces soldiers were sent to Syria.

Afghanistan

"President Obama responsibly ended the war in Iraq and will end the war in Afghanistan in 2014."
Sources: BarackObama.com

Remember Afghanistan? Our combat mission there came to a "symbolic conclusion" in 2014, but combat troops remained.
As it stands now, combat troops will remain in Afghanistan into 2017, and just last week our combat mission in Afghanistan was expanded.

The United States has carried out at least a dozen operations — including commando raids and airstrikes — in the past three weeks against militants in Afghanistan aligned with the Islamic State, expanding the Obama administration’s military campaign against the terrorist group beyond Iraq and Syria.

Obama has extended and expanded the combat mission in Afghanistan far beyond the end of his presidency. And when I say "far beyond his presidency", I mean exactly that.

America's 14-year project to defeat the Taliban and build a stable Afghanistan is teetering on the brink of failure, according to a sobering report Friday by a government watchdog.
The Taliban controls more of the country than at any time since U.S. troops invaded in 2001, notes the quarterly report to Congress by the Special Inspector General for Afghanistan Reconstruction. The fragile economy is worsening.

It appears much more likely that the narco state government of Afghanistan will fall before ISIS and the Taliban are defeated.

Libya

“It was very easy to break Libya, just like it was very easy to break Humpty Dumpty”
- Alan J. Kuperman, professor at the University of Austin who has cited the U.S. war in Libya as an example of how not to intervene

Nowhere are the repercussions of this military escalation more serious than in Libya.

“It’s fair to say that we’re looking to take decisive military action against ISIL in conjunction with the political process” in Libya, General Dunford said. “The president has made clear that we have the authority to use military force.”

Special forces units have been operating in Libya for months. The president is ready. The military is ready. So what’s missing? Something important. Oh yeah!

You wouldn’t know it from the presidential campaign, but the US is preparing to start military action in Libya … again. And given that Hillary Clinton was the leading proponent inside the Obama administration for bombing Libya and regime change the first time around, this should have a direct bearing on the presidential debate. Should, but hasn’t….
Instead of discussing expanding the still-undeclared Isis war to a third country in Congress, where the debate belongs, it’s being leaked to newspapers by anonymous officials and treated as an inevitability. And no one is giving second thought to the fact that constitutional scholars across the political spectrum consider such a move illegal.

Illegal is such a relative term. And by relative, I mean that the law is relative to the amount of money and political power you have.
The expansion of the war to Libya is troubling both because it is clearly outside of any congressional AUMF, and also because it has the potential of spilling into other countries.
Not a single presidential candidate has voiced concerns about this dangerous trend.

It also leaves open questions such as "...and then what?" After bombing ISIS in Libya, who is going to fill that void? Ansar al Sharia?

Everywhere else

In October 300 special forces troops were deployed to Cameroon. In November U.S. special forces troops were deployed in Mali.
It wasn't notable because U.S. special forces are in so many nations that its easier to count the nations they aren't deployed in.

“In the last decade, Green Berets have deployed into 135 of the 195 recognized countries in the world. Successes in Afghanistan, Iraq, Trans-Sahel Africa, the Philippines, the Andean Ridge, the Caribbean, and Central America have resulted in an increasing demand for [Special Forces] around the globe,” reads a statement on the website of U.S. Army Special Forces Command.
In 2015, according to Special Operations Command spokesman Ken McGraw, U.S. Special Operations forces deployed to a record-shattering 147 countries—75% of the nations on the planet, which represents a jump of 145% since the waning days of the Bush administration. On any day of the year, in fact, America’s most elite troops can be found in 70 to 90 nations.

Two things about that. "Successes" in Afghanistan and Iraq? Our troops are in 75% of the nations on the entire globe.
Does that seem insane to anyone else but me? Isn't that by definition, an Empire?
What's more these deployments are not peaceful.

On December 6, 2014, approximately 36 of America’s top commandos, heavily armed, operating with intelligence from satellites, drones and high-tech eavesdropping, outfitted with night vision goggles and backed up by elite Yemeni troops, went toe-to-toe with about six militants from al-Qaeda in the Arabian Peninsula. When it was over, Somers was dead, along with Pierre Korkie, a South African teacher due to be set free the next day. Eight civilians were also killed by the commandos, according to local reports. Most of the militants escaped.

We've had a backdoor increase of 145% in troop deployment under Obama (not to mention an increase of drone strikes by ten-fold).
Can we finally stop pretending that Obama is any less warlike than Bush was?

What do we hope to achieve?

Through 15 years of war the only thing we've proven is that we can break things. Afghanistan, Libya, and Iraq, we've broken them all (while helping to break Syria and Yemen), and all we have to show for it is piles and piles of dead bodies. Every single one of these nations are worse off now than before, and the more bombs we dropped the worse things have become.
What's more, the more we destroyed those nations, the more terrorists have sprung out of the ground. Yet our political dialogue has been limited to either 1) "we have to do something", or 2) "let's kill some bad guys".
No depth, No critical analysis of what has gone wrong. It doesn't take a lot of intelligence to see our mistakes.

In Afghanistan we empowered corrupt warlords. Those are our allies, and Afghanis resent them.

Instead, in the name of promoting democracy, the West has cynically supported fraudulent elections, endemic corruption, and warlord cronyism.
The West’s response to this has been to turn a blind eye, because the corrupt regime we’re backing there by definition constitutes "the good guys".

In Iraq we empowered a brutal sectarian government. This has led to the nation splitting apart, a condition now that is now permanent.
In Libya we helped destroyed all government institutions, and allowed tribal militias and jihadists to take over in the security vacuum.

In March 2011, Nato-backed Libyan rebel leader Abdel-Hakim al-Hasidi openly admitted that al-Qaeda jihadists who had fought Western troops in Iraq were fighting on the frontlines to topple Gadhafi. “Members of al-Qaeda are also good Muslims and are fighting the invader,” he said.
According to former CIA officer Bruce Reidel at the time, “There is no question that al-Qaeda’s Libyan franchise, Libyan Islamic Fighting Group, is a part of the opposition. It has always been [Muammar] Gaddafi’s biggest enemy and its stronghold is Benghazi.”

In Syria we armed jihadists in order to enable regime change, and bombed the jihadists to prevent regime change at the same time, an obviously insane strategy that only Dr. Strangelove could think up.

It would have been hard to screw up more completely without intentionally trying.
In every case we made the assumption that stable governments spring from the ground organically out of the rubble of war and destruction, rather than out of hard work, sacrifice, and shared interests. It's as if Washington doesn't even understand how public institutions work.
I can't help but notice that our broken foreign policy seems to directly reflect our broken political system.