Help this old rookie with speakers

Hi, @tbick . Welcome.

As a Boston Acoustics and Klipsch dealer for decades, I am very familiar with both. Your ears (and brain) have become quite at home with the Bostons. Like a pair of old comfortable slippers. I’m a Klipsch fan (currently do performance modifications), but, if possible, I’d suggest you put a pair of your model of choice in your room and spend some quality time with them. They will sound quite different than the Bostons. You may love them from the first note, or it could be a classic example of "mission creep" -- room acoustics -> cabling changes -> upgraded front end, etc to get just the sound you’re looking for. It will all be worth it in the end. Just don’t expect "the perfect sound" when you first power them up. Break in time matters (with new speakers), but you should get a pretty good feel for their personality within a few hours.

Good luck.

Who would buy speakers because the resale value is high?  I would buy what sounds the best to you and keep it.

Everyone has a sound they are looking for based on their goals. From your selections it appears you like the horn sound.  I get it, my dad made his own Klisch horn speakers.  Go listen to them and maybe some other speakers such as B&W or other.

Good luck

I would look at Klipsch line of active speakers and it comes with NEW amps, NEW preamp, NEW DAC, inside the speaker. Just connect your source (s) and you are in business. Check out The Nines:

https://www.popsci.com/gear/klipsch-the-nines-powered-speakers-review/

I have Crites Type B. 4 yrs old.  They are made with quality components.  Set up correctly, they will sound quite good.  I have subs and they sound better.  You can order them with ALK adjustable crossover now.  I have seen veneered versions that are beautiful.  These are the size of Klipsch Cornwall.  Half the price.