I fly Hueys for a living and our sim is pretty good, for a sim. It has a few flight model issues though that bug me but most people wouldn't notice. I actually had my girlfriend practice on it for hours with VR and a proper cyclic and collective control and took her up in a bell 206 to give her a flight lesson. She did no better or worse than an average students flying a helicopter for the first time although she did say she thought it helped her grasp how to use the pedals quicker. Also I can say my skill as a pilot does not directly translate to skill in flying the Huey in DCS.
As far as jets go though I'd put my money on the L-39 being most likely to let you go from no flight experience to being able to fly the real one and the Yak for props. As good as the sims may be on ww2 i don't see any of them teaching a first timer how to handle thst much power.
As to the best helicopter its probably between the Ka-50 and the Mi-8. The closest experience I have to either of those is a CH-46 (and not a whole lot of experience with it) but the ka-50 does feel like a multi rotor system with a lot of stability control systems and the Mi-8 just "feels right" but I don't have any experience with heavy single rotor helicopters.