If I lost all my saws again (lost 4 once n a fire and that's all owned at the time) and were to buy new they'd be: a ported MS241, a ported 60-70cc saw, and a ported 395xp. I love my 9010, but it's a bit hard finding parts for, so it's likely going down the road soon. I personally love my 562xp Husky and really like Dolmar/Makita 6100's. a 462 wouldn't hurt my feelings at all though.
For your situation, best bang for the buck: Step 1: Port the 661 and buy a Stihl 25" (actually 24") bar for your 661 and have a good laugh while quickly bucking smaller pieces. Now you hae 2 bars sized for different applications, and les teth to file for smaller wood. Step 2: sell the 290 to buy either a MS241, MS261 or Husky 550xp (any of them ported), then IF you still need/want a middle option, try a few and make a decision leading to step 3.
In the mean time, you have a bucking/felling saw and a canopy saw. I have 10 saws right now, but usually a firewood outing for me sees my MS201T, a 50cc saw (I have 3), and a 60-70cc saw (I have 3). If I need bigger, I have a ported MS660 and Ported 9010 to choose from. The 10th is a McCulloch that belonged to my Grandfather, that I keep for sentiment, and to remind myself why I appreciate newer saws. Google McCulloch 35 and you'll see why. On the note of chains, you can't have too sharp of a chain, and that's the single best mod you can make to any saw.
Good luck, and always ask questions, as earning the easy way hurts the body, mind and pocket book much less than the hard way!!
A few pics for reference:

The 034 Super in the pic below isn't mine, but a friend's recent acquisition from another friend of mine. This was a rare instance where I didn't use any of my Huskies. L-to-R: MS261, 034 Super, Ported MS660, MS201T (all of them at least muffler modded and timing advanced) I used both my 24" and 36" bars on my 660 that day, and it had the 24" for that picture. It's always nice having options.
