1st post in this thread for me. These are the planes I enjoy flying the most, although not necessarily the ones I fly the most. However, I play FSE and own my top 2 planes in that universe, so I do fly them more than the others.
#1. TBM 930: This is plane is perfect for my favorite type of flying. That is, touring the world at a reasonably fast speed in all weathers, and with great short-field performance even high and hot. And with this plane, I can make decent money in FSE doing exactly this. In FSE, I’ve flown mine all over North, Central, and South America, plus the Caribbean, crossed the Atlantic via Ascension Island, been all through west and south Africa, then up across the Sahara to the UK, from which I went on a European tour. I just LOVE flying this plane. It triggers my inner Jeremy Clarkson despite not being a jet.
#2. MilViz C310R: I also own this plane in FSE and I got it specifically as a change of pace from my TBM. If I’d gotten the 414 instead, there wouldn’t be that much difference. I play FSE in a similar manner with this plane but must work with only 2/3 the speed and 1/2 the altitude. Also, this plane is MUCH more challenging just to land (as it has a higher approach speed with literally no margin for error. And the whole product is so good and the sounds are so, so awesome, which is good because I have to listen to them for hours. For instance, my last flight was 850 miles from Las Vegas to Cabo San Lucas, and I still had 41% fuel left at the end. This plane can go 1200-1300 miles with a reserve and full seats.
Now we get into things I might not fly so much but still love.
#3: Wing42 Blériot XI. This is a study-level plane that has essentially zero systems. It has no instruments, nor a panel for them, nor a firewall, nor a cockpit floor, nor even a seatbelt. Nor ailerons, nor trim, nor a proper throttle, nor brakes. The difference between stall speed and Vne is very small and you have nothing to tell you where you are between them. If you think you’re an aviator, not just a pilot, then prove it with this plane. It’s just you and the seat of your pants.
#4: Wing42 B247. Seriously, you gotta love any plane where, if you don’t like what your gauges are say, you can tap them and the needles move a little. Starting the plane requires physical effort both winding up the flywheels and hand-pumping the fuel pressure. It doesn’t have circuit breakers, it has fuses you have to change out (while hopefully figuring out why the fuse blew). And this plane also introduced an entire global radio navigation system new to the game but very, very old to the real world, which is fun to use. It makes you appreciate VORs and even NDBs more 
#5: CTLS (or is it really CTSL?) This is just a fun little plane all around. It can do a Cuban-8 right off the runway and it has a negative flap position for what passes for speed in the thing. And you have all these big windows and no wing struts so is great for observing new POIs on the ground. One of my favorite things about it was that, until a recent update to the Garmin Aera, it had no attitude indicator, which made it IDEAL for drunkenly flying into hurricanes 
Now you can let the visual horizon go for a while thanks to the Aera, so it’s not quite so fun although good winds still blow the little thing all over.
Seriously, this plane is something of an outlier in the whole Citation family. Mostly because it’s the only one that doesn’t have the trademark barrel-shaped (or are they really coffin-shaped?) windows. Seriously, whether a Citation is one of the original few marks, a CJ-whatever, an XLS, a Sovereign, an X, a Latitude, or a Longitude, very few of which have any real family resemblance, they all have those windows. Except the Mustang, which has little, squinty windows.