Best time: Defo pre-colonial era 19th century. This when all the major, major clan feuds began to take a rise. It was also extremely violent, with nomads traveling as far as 1000 miles to settle tribal scores and expand into different territory. Also, majority of the gabays were made in this time period.
Worst time: Without a doubt, the Somali civil war that began in the late 80's to 90's. Subxaanallah, many, many people died during that tragedy from all corners of Somalia. It was a bloody, horrific civil war which should be repeated ever again, hopefully. It's also the reason why we are on welfare in a western country.
Worst time would probably be in the civil war. Best time is now. I have water, electricity, roof over my head, meal on the table and clothes on my back.if my parents never left somaliland there would be a likehood I wouldn't live such a complete life. Alhamdulilah for the west which let my family migrate for a better quality life.
In a diaspora sense the worst time was during the 90s and the best is currently but I would say (2016-2019) because that was when Somalis were in everything and everywhere you would go you would see a upcoming Somali on social media (Halima, Ilhan)
In the diaspora, mid 2000's to early 2010's was the best. Late 2010's - present day is the worst. Somalis were better off as an obscure and unknown minority group. The fruits of the dysfunction and sins of our predecessors are on full display with no coming back. It's going to steeply go down here from now.