If public postures are a guide, both sides will wrangle over borders and water rights. They will consider using foreign peacekeepers, including Americans, to safeguard a demilitarized zone. They will look to Washington for massive aid and even argue over what the word peace means.
With Israeli-Palestinian talks under way simultaneously, opportunities to play one side against another will be complex, tempting and aggressive.
"There's going to be a hell of a ride in the next few months in Arab-Israeli diplomacy," said Rob Satloff, executive director of the Washington Institute for Near East Policy, a Washington think tank.
Some of the obstacles that Syrian and Israeli negotiators must overcome:
Territory. Determined to recover the Golan Heights, which Israel annexed in 1981, Syria has already won much of the battle. The debate in Israel now centers less on whether to return the 452-square-mile parcel than on the terms for handing it back.
In addition to its strategic location - overlooking northern Israel and about 40 miles south of Damascus - the Golan has etched itself into Israeli hearts as a beautiful mountain resort. Its 18,000 Israeli settlers are less militant than those on the West Bank, and Barak figures that most Israelis are willing to trade the Golan for a durable peace.
Establishing new borders may be tricky, however. Syria wants to return to the borders that existed on the eve of the 1967 war; Israel is insisting on "adjustments" to address water and security concerns.
Security. Israel's worries are numerous. It has a sophisticated eavesdropping facility atop Mount Hermon, the Golan's 6,900-foot peak, to provide warning of a Syrian attack. Israel is loath to abandon that facility, which also enables it to spy on Syria. Israel might let it be staffed by Americans or another third party.
Israel also wants fewer Syrian troops between the Golan and Damascus, the Syrian capital. That demand could prove sensitive for Syrian President Hafez al-Assad, who for decades has defined his nation and motivated his troops - the ultimate guarantors of his power - by maintaining an unyielding stance toward Israel.
Both sides are likely to accept an international monitoring force - probably including U.S. troops - in a demilitarized border area, similar to the one in the Sinai Peninsula between Israel and Egypt.
Israel will count on Assad to curb terrorist attacks from Hezbollah, the Iranian-backed militants based in southern Lebanon. Experts say Assad's reputation for ruthlessness, as well as the 35,000 Syrian troops in Lebanon, can rein in Hezbollah.
Nature of peace. Simply by negotiating with Barak, Syria has handed Israel a victory, implicitly recognizing its right to exist. But Israelis - bitter over limited ties to nominally friendly Arab neighbors such as Egypt and Jordan - want a "warm" peace, with the exchange of diplomats, trade, tourism and open borders with Syria.
Assad, who presides over a largely closed society with an effective secret police force, is troubled by the prospect of opening up to democratic and entrepreneurial Israelis, analysts say.
"The Syrians are concerned whether this is opening the door that brings down the system," said Jon Alterman, a program officer at the United States Institute of Peace in Washington.
Water. A commodity especially precious in the arid region, water factors into calculations for setting the Golan's borders. Syria's effort to return to 1967 boundaries would bring its territory to the edge of the Sea of Galilee, which supplies about 30 percent of Israel's fresh water. Israel balks at that.
Two tracks. Barak seems unfazed at having to negotiate simultaneously with the Palestinians and the Syrians; he has set a tight timetable for reaching accords.
Some analysts believe he will use the two tracks to advantage - dealing with whichever side is more willing to compromise and trying to use progress on one front as leverage on the other. Both Assad and Palestinian Authority Chairman Yasir Arafat are believed to be eager to reach an agreement before age or illness sidelines them or Israeli and U.S. officials lose their enthusiasm for a deal.
From a security standpoint, striking a deal with Syria is more important to Israel. But Arafat may hold the last card, analysts say. Barak wants to present a referendum to Israelis on a comprehensive peace deal; he cannot deliver that until he addresses Palestinian concerns.
Outside aid. The United States has pumped more than $100 billion into the Middle East in the two decades since the Camp David accords brought peace to Israel and Egypt, which are the first- and second-largest recipients of U.S. aid. Syria, whose per-capita income has dropped 20 percent in the last four years, may be hoping for a peace dividend.
U.S. officials say it is premature to discuss what contributions they might make to support an Israeli-Syrian peace accord. Syria remains on the U.S. list of nations that support terrorism.
Others say that Clinton might promise aid and leave his successor and the next Congress to wrestle over the cost.
In a little-noticed move, the administration last week welcomed the first trade delegation from Syria to the United States in 30 years, signaling perhaps that American trade - not just aid - might sweeten the pot for Syria.
Nomi Morris in Jerusalem and Joyce M. Davis contributed to this article.