Circling back to the OP's thoughts about the MS250/MS290 combination...about fifteen years ago, I got into cutting down orange and avocado orchards. Since there was only a Stihl dealer in town...and he's a friend of mine... and since my opinion at the time was that Stihl and Husqvarna were probably the best saws on the local market...my mind hasn't changed, the other ones folks like aren't really available around here...I went with the MS250. 16" bar as my go-to saw. I bought several...one used, three or four new, and at the time, I had some partners in the business. Those 250s, including the used one, NEVER gave us a lick of problems! Still haven't, although we moved on from the business and I still use that saw fairly regularly, but not as much as before.
To round out the combo, I got a MS290 with a 20" bar. I'm thinking the percentage of use was 80% MS250, 20% MS290. Again, NEVER a problem...until a month ago...when my son-in-law, know-it-all, entitled Millennial that he is, burned it up...probably ran it out of chain oil, kept goin', or just simply didn't let it rest a little, who knows? It's back up and running now, with the MS390 engine from Bailey's in it...
But for pretty heavy use, this has been a good combination. I think I'd step up to the MS391 for the extra power over the 291, staying in the intermediate level of what I reckon they call 'farm/ranch' use. I've never felt that the 'pro' level was where I needed to be, and I was cutting pretty heavy back in the day.