For the second time in four years, Oakland’s Port Commission this week is expected to enter into exclusive negotiations with the Oakland A’s for a possible ballpark at Howard Terminal.

The first exclusive negotiating deal in March 2014 ended within months, after the team’s then-managing partner, Lew Wolff, backed by Major League Baseball, concluded the waterfront site wasn’t viable.

The new discussions come amid signs the A’s are feeling increasingly hopeful that they can make a ballpark work on the 50-acre property north of Jack London Square — despite a slew of transportation, environmental and regulatory hurdles that deterred them in the past.

The first step will be a “feasibility analysis” to address both the challenges and what it would take to get the needed approvals from State Lands Commission, Bay Conservation and Development Commission and other regulatory agencies that have jurisdiction over the port.

Oakland Mayor Libby Schaaf has likened the talks to an “exclusive dating” agreement where both sides agree only to talk with each other.

And Schaaf said she “loves — just loves” the A’s idea of an overhead tram to shuttle fans between downtown Oakland and the site.

It’s no marriage yet, but it’s a start.

San Francisco Chronicle columnists Phillip Matier and Andrew Ross appear Sundays, Mondays and Wednesdays. Matier can be seen on the KPIX TV morning and evening news. He can also be heard on KCBS radio Monday through Friday at 7:50 a.m. and 5:50 p.m. Got a tip? Call (415) 777-8815, or email matierandross@sfchronicle.com. Twitter: @matierandross