Providing a safe and secure election environment will be the first big test for the newly empowered Liberian security forces, who remain under-equipped and underfunded, the UN says.
Olof Skoog, chair of the UN's Peacebuilding Commission for Liberia, told the Security Council in June that there were "real hurdles ahead" following the security transition.
Skoog cited "issues pertaining to land use, decentralisation, access to justice, and violence against women" as the key flashpoints in Liberian society beyond the election period.
A question of economy
Every candidate has asserted they have the magic formula to turn around Liberia's stuttering economy, which remains stubbornly reliant on foreign assistance despite significant endowments of iron ore, rubber and palm oil.
Boakai has campaigned on "roads, roads, roads", blaming the dire state of Liberia's transport network for a lack of development, while telecoms tycoon Benoni Urey has said agriculture must be developed to end a dependence on foreign aid.
The biggest shock to the economy during Sirleaf's tenure was the Ebola crisis that hit in 2014, virtually shutting down businesses, compounded by the collapse in commodity prices.
However, the African Development Bank said in a May briefing that investment in electricity provision under Sirleaf "should begin to gradually alleviate a significant constraint to the business environment".
Just over a fifth of the 2.1 million people registered for this election are aged 18 to 22, according to official figures.
Attracting enough of the youth electorate could sway a candidate's entry into the runoff election that will be called if no single candidate gains more than 50 percent of the vote.
In such a crowded field without a clear frontrunner, a runoff looks highly likely, experts say.
Young voters are concerned with unemployment and the state of the nation's higher education system, several candidates have said, with soft drinks millionaire candidate Alexander Cummings promising to overhaul vocational education.
Weah, a symbol of Liberian grit and talent on the football field, remains a revered figure among the nation's young people, and has also put education and job creation at the centre of his platform