the big one: how do you choose speakers? By what features, data?

My two cents is to figure out what type of speaker you are looking for first. Initially that is a question of floor standing vs bookshelf, ribbon, horn, planar, open baffle, box speaker etc. Then there are the different types of speaker voicings that are in some English or other foreign (to the US) countries that emphasize different things. 

Then research, research, research to find out the best in the categories you like, can you find those speakers to listen to?, price, performance, reliability etc. 

Obsess, obsess obsess over what you should do. Consider the price of the speaker and whether that would mean you have to invest in other things like stands, amplification, etc. What is the highest model you can afford and how long you can survive on macaroni and cheese before getting sick of it? Do the sellers allow for in home trials? 

Compulsively pull the trigger. Be happy for a year or so. Rinse and repeat.

@grislybutter

My order of preference in deciding on speakers is

1) Sound

2) Price

3) brand/company’s reputation

4) compatibility with existing amp, etc.?

I do not care about:

• sensitivity
• crossover frequency

I have equipment that can handle the last 2 with ease.

@dz13 you are very passionate, and I am too, I just need a little more research (which usually informs me how little I know and that I need to do moooore research)

@mrpostfire 

1) I thought - or I wish to think - the specs sheet helps figure out the sound. 

I know it's like reading a recipe and thinking "man this cake tastes exquisite!"

@grislybutter,

Thank you for the kind words!

Mike

You have to know exactly what you like, something you learn after a lot of experience which usually means you are entitled to a few missteps. I like line source dipoles which limits the search dramatically. Add to that a penchant for ESLs and I am down to just a few choices. 

If you are limited to smaller point source speakers the number of choices can be daunting. If you are looking for speakers that "disappear" you will be more likely to achieve that effect with mini monitors on stands adding subwoofers. The most difficult part of any speaker is the enclosure. It is very difficult to keep any box from becoming a musical instrument, but is much easier keeping a small enclosure from doing same. Just because they are small does not mean they are not capable of prodigious output especially when equipped with subwoofers and a proper 2 way crossover. Everyone should hear Roger's LS3 5As with subwoofers, a jaw dropping experience.