As time passes support drops if you want to run current things, Elektron have said 10.12 minimum and the same applies elsewhere - if you are backed up or can clone or swap disks even then give it a go - High Sierra / Mojave was way better than I hoped and teh upgrade only saw a few casualties, but definitely no Catalina for me
There’s a price both ways, by doing the legwork/research you can minimise that risk, it depends what s/w you value - my hand was forced on a couple of occasions so the decision was easy/unavoidable with disk crashes and so on but it worked out well and I use Carbon Copy Cloner every week now