I worked on Woody plant species. During my sample collection in forest regions even though plants reached their maturation age there was no flowering in both male and female plants.
This is intresting question. Dioecy causes cross pollination hence the seed produced from dioecious plants is cross-fertilised. The seed progeny represents half-sib or full-sib family. The breeding method of these crops follows that of cross fertilising crops e.g. maize, papaya, onion etc. Depending on the reproduction nature of your crop and the desired type of cultivar to be developed you may use a suitable selection procedure established for cross fertilisers.
Generally speaking, it can be said that the dioecy does not give rise to any limitation. This will depend on the pollination system. If the species is anemogamous, there is no restriction on reproduction. On the other hand, if the species is entomogamous or ornithogamous, the dioecy will represent a handicap if there is any problem with the pollinating agent. In this case, the dioecy is unfavorable compared to the monoecy.