Wow. Toughie. Lemme see...
GA.
I've got Carenado's Cessna C-152, Alabeo's WACO YMF-5 and Cessna C-188 AgTruck, Bill Ortis's Piper Pacer/Tripacer pack, Flight 1's Cessna C-177B Cardinal, and Just Flight's Piper PA38-112 Tomahawk, as well as several freeware offerings. I'm a big fan of Alabeo's WACO, and I'm eagerly awaiting to see what they come up with in their rendition of the Piper Tomahawk (I would LOVE to see Alabeo do a Cessna A152 Aerobat with a tailwheel conversion), but out of this group I'd have to say the Just Flight Tommy is my personal favourite so far. The VC looks great - as do the externals - she flies nicely and is easy to trim out for level flight, and I'm a big fan of the real world aircraft to start with. A very close second is Rick Piper's freeware Aeroprakt A22 Foxbat, just because it was modeled so well.
I'd really like to see some more LSA's, though, as that segment of sport aviation has just exploded. If William and his Lionheart team decided to this little number below, the Tomahawk might have a serious rival for my affections...
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Military:
Not much into military stuff anymore. I have a couple payware examples (RealAir's Spitfire - the PR.XIX surprised and punished me for my inattention for not throttling back after takeoff by blowing up its Griffon and doing something rude with its oil all over my windscreen, but lesson's learned...), and I have a couple of other pay and freeware pieces, but my go-to warbird has become the revived Wozza/FSDS AT-6 Texan/Harvard/SNJ ever since John Terrell worked his magic on the FDE file, as well as producing some spectacular paint schemes and paint kit for it. Bravo, John! And thank you!
The Six is also a personal, real world favourite having spent several memorable flights in them...
Helicopters:
Don't really fly them much in FSX or FS9 for that matter. I am debating getting the Aerosoft Bell 205/UH-1 Huey as I'm such a fan of that iconic aircraft; just the sounds of the start-up gives me the shivers. I'm sure other Huey-philes will agree...
The big reservation I have with FS helo's of any description is, of course, control set-up and limitations. Short of having a rig with cyclic, collective, and anti-torque pedals, I kinda feel helo's are something of an odd man out, FS-wise. But that being said, I'd love to see someone model the Rotorway 162 with a JetExec turbine conversion (Rotorway had announced their own certified, Rolls-Royce turbine-powered 300T back 2009, but little seems to have come from the project. Current 162 Exec turbines commonly employ 150 shp Solar T62 surplus turbines which led previous lives as APU's and ground power units). An FSX native of the gargantuan Russian Mi-26 would be nice, too.
So there's my list. But no exercise like this would be complete without a personal wish list:
GA.
1)
Ultraflight eLazair electric-powered ultralight
2)
Aeronca 15AC Sedan (Hint, hint GAS

)
3)
Zlin Savage Cruiser
4)
FK Light Planes FK14 Polaris (Le Mans version)
And just for good measure...
5)
Micco SP26A
N.