To me, the one downside to Trailboss is you cannot achieve what I would call "mid-range" ballistics with it.
I see the need for a 400gr cast at 1,800 to 2,000 for a nice general purpose practice load - and you can't do that with the TB.
But no powder is perfect, and TB fills a niche.
5744 will probably work for you. I load resized 300g 44 magnum bullets in my 404. I asked Accurate for load data and they emailed it to me. My starting load got about 1700fps and I haven't seen need for more, but there was plenty of room to increase velocity if I needed to. Trail Boss makes for really gentle loads with the same bullet.