Griffin Seannery:
Currently watching Okaeri Mone (loved it so far) and not sure what to choose next.. Should I quickly jump in to Mai Agare? Or there are older titles worth trying?
So far I've watched Mare, Hiyokko, Manpuku from TV (which suddenly decided to stop airing Asadoras lol).
How did you like the ones you tried? I'm waiting for Mai Agare subs to be completed before watching, or at least nearly finished. Sometimes asadora subbing projects stop partway through, even for multiple years. Out of the ones I've watched that you haven't, I recommend Hanbun, Aoi the most, and then Natsuzora. The former in particular subverts a lot of asadora tropes in interesting ways, but both are really special. I also enjoyed Toto Nee-chan but it wasn't in the same tier for me.
The ones I've dropped after several weeks' worth of episodes are Asa ga Kita and Gochisousan. The characters in the former weren't engaging to me and the latter had an endless array of irksome characters to me. But there are lots of people who enjoyed both, so, you know, YMMV. :)