As the Dublin native seeks a divorce, his legal and financial situation may sound difficult, but this is not unusual in Ireland due to the country's divorce laws, which are among the most restrictive in Europe.
Under current legislation, which is enshrined in the country's constitution, a person can only apply for a divorce after living separately from their spouse for four out of the previous five years.
No one is exempt from this mandatory wait time, including those who are trying to leave abusive relationships, most of whom are women. Women suffering from domestic abuse could benefit from a shorter divorce process in order to protect themselves -- and their children -- from continued abuse from a former spouse, according to the National Women's Council of Ireland.
Other individuals in the process of separating, like Rossney, argue that the minimum wait time creates unnecessary levels of anxiety, prohibits their ability to move on, wreaks havoc on their emotional well-being and is a terrible financial burden.
That could all change on May 24 when Ireland goes to the polls in a referendum on divorce.
Voters will also be asked if they want to remove a law that doesn't recognize foreign divorces, a provision that prohibits people who divorced outside Ireland from remarrying.
Flanagan added that the government intends to reduce the living apart period to two years so that both parties can "move forward with their lives within a reasonable timeframe."
Forty-year-old Rossney told CNN that the long wait has fueled a hostile environment that has been exploited by the legal system, and that the proceedings -- and relationship with his ex -- could have been more positive if the mandatory period wasn't so drawn out.
"I don't think we would have hit such a low point if things hadn't dragged on so long," he said. "We knew we had a protracted war ahead of us."
Rossney, a proud father of two, said that he believes that the current law means that legal teams don't have "any incentives to stop fighting until the money is gone." He said that Ireland's family court "is not fit for purpose" as "like any other court, it is ... a fight until one party wins and theother loses."
Many in the process of divorce support the government proposal. If it passes, it will be the latest in a series of measures reflecting modern Irish society that have recently questioned, and rejected, the historical role of the Catholic Church's doctrine on its institutions.
While public support for the change in divorce law is high, a small minority fears that if it passes, it could lead to the demise of the institution of marriage.
David Quinn, director of the Catholic advocacy group Iona Institute, told CNN that if the waiting period was taken out of the constitution, "politicians will eventually vote two years down to six months, in which case the difference between marriage and cohabitation, legally speaking, becomes ever finer."
"There should be a kind of trip wire to really slow down and think about it," he added.
Quinn's comments reflect Ireland's difficult relationship with divorce, and the upcoming vote will mark the third time the country has held a referendum on the subject.
Almost a decade later, Irish voters were asked again. The 1995 divorce referendum was a hotly contested campaign, vocally opposed by the Catholic Church. Marked by prominent signs reading "Hello Divorce, Goodbye Daddy," anti-divorce activists argued that Irish men would leave their wives en masse if it passed.
Some of that lingering anti-divorce sentiment, coupled with the current legal restrictions and the rise in cohabitating couples, are reflected in the country's current divorce rate, which is among the lowest in Europe.
While the introduction of divorce has been viewed as a pivotal moment in Ireland's modern history, most of the Yes campaigners that CNN spoke to argue that the confines of the law continue to reflect an old Ireland, one whose constitution still has laws reflective of the Catholic Church's grip.
Bishop Denis Nulty, chair of the Council for Marriage and the Family of the Irish Catholic Bishops' Conference, said in a statement Saturday that "it is important to reflect deeply on the implications of this referendum which seeks to expedite the dissolution of marriage," adding that the government should "recommit resources to marriage preparation and invest resources into marriage enrichment."
David Graham, 37, who is currently separated, told CNN that when Ireland first introduced divorce, the "outside world might have thought Ireland had become more progressive. But when you look at it, it's more regressive because they put in stipulations to make it very difficult to get a divorce."
While he actively supports the upcoming referendum, he fears the new proposed wait time will still restrict separating couples' ability to move on at their own pace.
"You go through that process and you just want to get through it, and you want to move on -- but you're in a situation you can't move on."