Tad, if you have responsibilities, such as children, or parents, then the best is to maintain a daily meditation practice which seeks depth every time one meditates and work toward early retirement, as you are doing. In Asia it is common practice for the parents to retire and hand over the responsibilities to their children as soon as they are capable of doing so. Typically dad and mom retire at about 50, and their children take over the financial responsibilities at mid-20s to 30s. Grandma often takes care of the grandchildren while her kids work to support the extended family.
Otherwise, taking up the mendicant life seems better, when there is no monastic tradition that values and supports rigorous, self-aware contemplatives as we see today.
This is why I have lived as a mendicant for 18 years while working toward building a monastic community out of the supporters of the Great Western Vehicle.