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White House adviser Jared Kushner headed back to Israel and the West Bank this week in a renewed push to broker Middle East peace, just one of several responsibilities the administration has handed to President Trump's 36-year-old son-in-law.

Despite Kushner's unusually varied workload — he's also tasked with reforming veterans' care, solving the opioid crisis, something to do with “American innovation,” and more — this is his second trip to the region in the space of just three months. That may be a sign of how keenly the new administration is chasing peace between Israel and the Palestinians, which Trump has described as the “ultimate deal.”

A few months ago, there was actually some cautious optimism among Middle East watchers that Trump might be able to make some progress. Sure, he and Kushner don't have any diplomatic or political experience, but so what? Trump was a self-described dealmaker who didn't have much of the political baggage of his predecessors. The experts hadn't done so well finding a solution, so why not give them a try?

But that optimism has faded, and Kushner's trip has only highlighted the sizable obstacles he faces. Here are five of the biggest:

The Israelis

As The Washington Post's Loveday Morris and Ruth Eglash noted this week, a lot has changed in Israel since Kushner's last visit in June. A corruption scandal swirling around Prime Minister Benjamin Netanyahu has put him on the defensive, and a criminal indictment now looks possible. Some analysts think Netanyahu will refuse to make concessions that may anger the Israeli right — such as Jewish settlements built on the West Bank — to protect his political flank.

“Talk of scandal and indictment is swirling around Netanyahu and is pushing him to circle the wagons and reach out to his right,” Aaron David Miller of the Woodrow Wilson Center wrote for CNN this week. “Never a good omen for peace.”

Meanwhile, some Israelis grumble that the United States isn't taking their problem seriously. “We are not in the administration’s priorities. They are preoccupied with other issues, and there is a feeling that they have very limited attention span,” an unnamed senior Israeli minister said  to Jewish Insider.

The Palestinians

After Kushner's June visit, it was the Palestinians who were annoyed by the American. “They sounded like Netanyahu's advisers and not like fair arbiters,” one senior Palestinian said to London-based Al-Hayat.

Among the complaints is that Kushner won't publicly commit to a two-state solution in which Israel and an independent Palestine would exist side-by-side. In a confounding move, the State Department suggested Thursday that it could not commit to that solution, the one long endorsed by American, Palestinian and other international leaders, because it would indicate bias — a position that shocked some observers.

Such moves put Palestinian Authority President Mahmoud Abbas in a difficult position. He has conditioned his cooperation with Kushner's peace initiative on a public commitment to a two-state solution. And much like Netanyahu, the 82-year-old Abbas is looking politically weak at home, where there are widespread complaints that he has not made any gains in the peace process after twelve years in office.

The rest of the Middle East

Kushner's trip included meetings with a number of other Arab leaders, a recognition of how regional support will be needed for any peace initiative. Dennis Ross, a former U.S. envoy to the peace process, told the National newspaper of Abu Dhabi that because of distrust between Israeli and Palestinian leaders it would be “nearly impossible for them to do anything without an Arab cover.”

But the potential issues with that tactic were underscored in Egypt, where Kushner's trip awkwardly coincided with a surprise U.S. decision to withhold millions of dollars in aid from Cairo. The decision prompted a sharp statement from Egypt's Foreign Ministry, which said it reflected “poor judgement.”

This was just one example of the increasing complexity of regional politics. Although there was once hope that Arab states could form an uneasy alliance with Israel over their shared animosity with Iran, a still-running dispute between a Saudi-led bloc and Qatar threatens to overshadow any other diplomatic initiatives in the region.

President Trump

Given his past comments about Muslims, the president is a controversial figure in some parts of the Arab world. But in Israel he was largely greeted as an improvement upon his predecessor, President Barack Obama.

Then Charlottesville happened.

Trump's relationship with Israel has become far more complicated over the past two weeks, with some Jewish leaders criticizing Trump for what they see as a weak response to neo-Nazi violence in America. After Trump suggested there were some “very fine people” on both sides of the protests in Charlottesville, the front page of Yediot Ahronot, Israel's most-read newspaper, read “Shame,” summing up the attitudes of a fair amount of the population.

Kushner himself

Kushner was always a divisive choice for Middle East envoy given his personal ties to Netanyahu (the Israeli leader once slept in the real estate scion's bedroom while staying in the Kushner family's New Jersey home). But there's a bigger problem: No one can actually work out what Kushner's plan is.

In an off-the-record meeting with White House interns that was later leaked to Wired, even Kushner himself didn't seem sure of his course of action. “What do we offer that's unique? I don’t know,” he said, later suggesting that there may be “no solution” to the Israel-Palestinian problem.

If Kushner isn't even sure he can do the task he was given, its hard to see why anyone else should, either.

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