Speaker types- your preference and your journey?

Infinity 1001A  My first decent speakers, for my college dorm rooms.

B&O  I don't recall the model no., but these were their top of the line floor-standing speakers, 4-way, IIRC, with lovely rosewood cabinets and black metal stands. They sounded a little better than the Infinities, but were not really audiophile-level.

Magneplanar 2.5c?  My memory is hazy for the exact model no.  These sounded great if there was no strong bass frequencies in the music, but were thin when there was that kind of bass.

Apogee Duetta II  Still my main speakers after all these years.  Fantastic soundstaging like the Maggies, but much better bass response.  They were taken to the next level when upgraded by TrueSoundWorks a few years ago.  For my moderate-sized, asymmetrical listening room and musical tastes, I don't think there are better speakers unless the newer ribbon planar speakers are better--I haven't heard them.  No need for a subwoofer with the Duettas, although if I didn't care about the floor space needed, I wouldn't mind trying subwoofers.  I suspect the asymmetrical L-shaped configuration of the open floor plan would mean higher bass on one side than the other, but I suppose that could be adjusted.

For secondary systems in smaller rooms,  I've gone with mid-level floorstanders and an active bookshelf pair from Paradigm and PSB, both Canadian companies that produce high-value, good-sounding conventional speakers.  They're fine for me for background listening.

My first pair of speakers were home built floor standers built by my brother.  Not sure where he got the components, they sounded great when I was 14 and he gave them to me along with a cheap Symphonic receiver.  I used that system until I turned 17 and bought a Marantz 2270 in 1972.  I wanted a pair of JBL L100's but the sales guy talked me into a cheaper set of Electro Voice Interface A's.  They had a dome tweeter and a 10" driver and a 10" vent.  I had these for a long time but they eventually disintegrated and I didn't think they were worth fixing.  In the early 90's I went with a Luxman integrated amp, CD player and a nice 3 head cassette deck.  I recorded my own cassettes for use in my car, never bought a commercial cassette.  I added a pair of NEAR (New England Audio Research) speakers, conventional 3-way floor standers.  Great speakers for the money and are still in great shape.  Then in 2019 I purchased a set of Goldenear Reference speakers and a Naim Uniti Star all-in-one.  That's my system today, but got the itch again.  I use Sonos speakers in various rooms and my garage, meh, they're OK.

I was a sophomore in high school (1975) when I purchased my first speakers: a set of KLH bookshelf speakers.  Off to college and fell in love with a set of RTR 300D towers. Prior to graduating college I moved up to the RTR satellite subwoofer system - DAC1 and SAT1's.  My wife gifted me a second DAC1 subwoofer as a wedding gift (she's a keeper and has been for 44 years!).  The RTR subwoofers were truly ahead of their time with sealed chambers and passive radiators and tested flat down to 16 Hz. and they were like large end tables!  I've also owned AR, Martin Logan, Infinity and DCM.  Lastly I've settled on a set of Maggies - 3.7i with a set of REL S5/10 subs. Very pleased. 

Main rig speakers between 1981 - 1989:
1. Mariah LS-2
2. Energy Pro 22
3. Merlin 2B+
4. Merlin 4B+
Main rig speakers since 1990:
5. Sterling Acoustics Acumen II

Lots of mods, upgrades, and configuration changes over the years, but have had the same main speakers, tube amps, and tube preamp for over 35 years.

In your post you asked for us to explain what speaker type and preference of speaker do we prefer, and the journey. I’m going to stick to what you requested for us to answer in your post. 

So, I will start with the journey. My journey started at the age of 10 when I heard the system my oldest brother Rick had at the time... for the first time. This post is about speakers so I will stick to the topic and not go into explaining what his system consists of. The speakers are ALTAC HORNS that he had placed in each corner of the room out away from the corner and the sides of the walls about 2 feet from the back and side walls. I don’t know what model the speakers were, but they were very large speakers that he had acquired from a public movie theater remodel. Those speakers sound filled our very large basement with music that was carpeted wall to wall, and it was wide open that ran the length of our house. The sound was Amazing... So amazing that I became a fan of the way music could sound that day at the age of 10. Believe it or not I think I may have become an Audiophile that day. I always loved the sound of music, but that day changed the way that I would hear and think about the sound of music. So, to make a long story short I will skip a few years and go ahead and get back to the topic of the post. 

My first speaker that I actually purchased was Acoustic Research AR 3a after saving up enough cash to get them in the mid 70s. By this time I was just turning 15 yrs old. After loving the sound of the ARs so much, I was hooked to the type of speaker that they were. The type was an Acoustic Suspension Sealed Speaker. I was hooked on the crisp and tight sounding deep bass that they produced from the sealed encloser. So, my preference of speaker became SEALED SPEAKERS. I keep those speakers for many years in my main system, and I still have them to this day, along with an even more impressive speaker the Waish 4000-tall Ohms Acoustic speakers that I was given to by my uncle who was a true Audiophile from back in the 50s that had passed away in the 80s and he told his wife my ant to give them to me if he passed away. Thank You, Uncle Alfrad... RIP . They are not in my main system although they are still operating in my vintage system room. In my second system room I have my Wharfedale Jade 3 stand mount speakers. The Wharfedale jade 3s are also sealed and have a very strong tight bass response. So, sealed speakers are my favorite type of speakers for Critical Listening. But I have speakers that are ported also that I like very much with amazing dynamics such as my Borresen X1 stand mount speakers that I purchased recently about a year ago. Also, of the ported design my Mission 770 mk2 that I purchased in 1980 that are in my vintage listening room and sound amazingly great and are in mint condition due to being in an Air Quality Climent Controlled room from the day of purchasing them until this day. To wrap up my response to this post, I have many speakers that I switch around from time to time that I go to when I get interested in hearing another sound signature or a different tone of sound in the same rooms. 

GOOD DAY & PEACE TO ALL