In 2003, Bailão worked as an assistant to Ward 18 Councillor Mario Silva and put her name forward as a candidate to replace him in the election that year, running on a platform focusing on environmental issues, tenants rights and reduced property taxes for seniors.

She described herself as "centre-left, maybe centr[ist]", running on a campaign of efficient service delivery and community involvement in decision making, and won the ward.

[14] The symposium was among the first major undertakings to examine the then emerging inequity evolving between various income strata and the impact of this dynamic upon the city's neighbourhoods and housing sector.

[15] 2011 saw the City of Toronto contending with significant financial pressures,[16] coinciding with a reduction of funding from both the provincial and federal governments with respect to housing.

[21] Excluding the 11 homes that had already been approved for sale by city council in previous reports, the TCHC Board recommended an additional 675 units be sold.

[26] In response to these concerns, Bailão requested the opportunity to lead a special housing working group[27] in order to identify innovative solutions and creative partnerships.

In its meetings on March 5, 6, and 7, city council approved Bailão's request and she was appointed to lead this working group along with management consultant Jim Pimblett, TCHC Board Chair Bud Perves and former cabinet minister Alan Redway.

This working group was asked to report back to Executive Committee in early fall, 2012, in order to provide recommendations to city council.

[36] In March 2013, another of the Special Working Group's recommendations was implemented and realized when $93.5 million was unlocked as part of the refinancing of 18 mortgages at lower rates through Infrastructure Ontario.

[38] The approval by city council of the mortgage renegotiation also marked a significant achievement for the Special Housing Working Group's report.

In addition to the already implemented recommendations from the Special Working Group, the original target of raising $120 million towards the repair backlog was achieved in only the first 6 months of the report receiving council approval.

[40] The end result of this work and advocacy was a 10-year state of good repair plan that included a $1.3 billion investment over the decade from the federal government in addition to funding from the City.

[52] In September 2022, the Building Industry and Land Development Association honoured Bailão's work in addressing housing supply and affordability.

[56] Bailão also discussed expanding cellular service in the TTC subway system, describing it as a "convenience and safety issue", and stated that telecom providers have a "duty" to work with the city, which major firms have refused to do.

[56] Bailão joined Canadian real estate company Dream Unlimited in January 2023 as the Head of Affordable Housing and Public Affairs.

Mayor Rob Ford commented on the incident and said, "Ana is a good local councillor, she works hard and represents her residents well at City Hall.