These three items on Lee's to-do list are almost assured, but anything more than these items is fraught with risk.
Lee's task is to pursue the seemingly irreconcilable objectives of nudging Trump to stay engaged positively with Asia while at the same time avoiding offending an increasingly prickly China. Higher ambitions -- at least on the public front -- present the serious risk of something going spectacularly wrong.
Effusive praise from the American President is the stuff that politicians usually crave, but in this case, it would risk undoing the "good work" Lee did his recent visit to Beijing
, where he seems to have been provisionally forgiven for his earlier lack of respect, much of which centered on Singapore's role in promoting the American position over China's activities in the South China Sea.
In the second half of 2016, the Global Times and the People's Daily -- an unofficial and an official mouthpiece respectively for Chinese regime -- ran articles critical of Singapore and Lee Hsien Loong personally, for engaging Japan against China in the South China Sea
, and declaring Singapore's alignment with the official US position.
Behind the scenes in America, Lee and his entourage are likely to be on much more comfortable turf as they continue their long-term and highly successful engagement of the American foreign policy establishment and the American business community.
Singapore's entire national leadership is at home walking these corridors of power, since most of them have studied, socialized and networked in them for decades -- with PM Lee himself having studied in the United States Army Command and General Staff College in the 1970s.
It is difficult to imagine a national leadership anywhere in the world more in sync with Washington than Singapore's -- at least on international issues. Yet this is where their problems with China begin.
The current generation of Singapore's leaders -- right down to the upper levels of the civil service -- is so close to the Americans that they give the appearance of having mistaken the American establishment view for their own.
Take, for example, Singapore's leadership in standing up to China in the South China Sea, which it undertakes despite Singapore itself not being a party to any of the South China Sea disputes. China took particular offense in 2016 when Singapore's leader Lee used another visit to the US to criticize China for winning friends by handing out "lollipops" to poor countries -- and then urged America to do the same. "You do not do things which the Chinese do" he told the Americans.
"The Chinese go around with lollipops in their pockets
. They have aid, they have friendship deals, they build you a Prime Minister's office or President's office, or Parliament House or Foreign Ministry. For them, trade is an extension of their foreign policy. You do not do these retail items," he said.
The height of China's backlash against Singapore came late in 2016 when it impounded millions of dollars-worth Singapore's defense equipment
for several months as it was passing through Hong Kong harbour on its way back from exercises in Taiwan. And just as that was impasse was being resolved it emerged that Chinese President Xi Jinping explicitly refused to invite Lee
to the Belt and Road Forum in May 2017.
Between them, these Chinese actions threatened Singapore's medium-term future in a way that could not be ignored -- and to a degree that even overshadowed the benefits of American friendship.
The worst of the damage was undone in the lead up to PM Lee's official visit to China last month when Lee gave an interview with Chinese state media
. In the interview, he praised China's development, stressed the strong ties between the two countries and listed a number "meaningful" joint projects.
"China is a big country, is a very complicated country, governance China has never been a simple matter. But there is such courage and unity, China will certainly overcome all difficulties, certainly continue to develop, continue to move forward," he said.
As a result of agreements signed off during the visit, Singapore is part of One Belt One Road
again, but it would not take much to disturb the relationship all over again.
China's petulance has reinforced the Singapore leadership's conviction that it needs the US in the Pacific and in the South China Sea as a balance to China, but how to work for that cause without inflaming China all over again?
This is PM Lee's dilemma, and unfortunately all of his US-centric training and experience and networking makes him particularly ill-suited to working through it. Dealing with both Xi and Trump would have been a tough enough problem for any Singaporean leader, but thanks to his earlier blundering, he now needs to tread with particular care.
Hence, a quietly successful trip that can be played up to his domestic constituency is very much the order of the day.