I have an '09 Genuine Stella inn olive green and love it. I had wanted one for a long time, and finally bought one as the 2 strokes started to disappear. It sure beats the plastic twist and go scooters. Be careful however, it is not as reliable as some of those Japanese scooters. My engine seized at just over 300 miles, reason unknown, repaired under warranty. I have since had a local vintage Vespa shop build me a "bulletproof" engine for it, and have had no more issues.
The Royal Enfield has similar reliability issues, but so did other bikes from back then. I used to own a '66 Triumph Bonneville. It spent more time getting worked on than ridden. But it had character and soul, something the modern Bonnie, TU250, W650, W800, GB500, etc. lack. The W800 is not available in the U.S., the W650 and GB500 are next to impossible to find, and if you are lucky enough to find one, the seller will want as much for it as a new Bonneville. The one bike on the list that still has character is the Sportster 883. It is crude, primitive, very basic and elemental, AND it vibrates like crazy and makes the right sounds, something more refined bikes like the new Bonneville lack. It is reliable, and parts will always be available for it. It is not big, but it is heavy, because it really is mostly made out of metal. If you were seriously looking at Enfields, the Sportster is your bike. The one thing that might turn you off to it has nothing to do with the bike itself. It is the Harley image, culture, scene, whatever. If you like it, fine. If you don't, you can ride a Harley without being a part of it.
I won't spend more on a bike than I think it's worth, but if it's a good deal, I don't seem to have a problem buying bikes I don't need.
2002 Vulcan 750, 2013 Royal Enfield B5
2001 XT225, 2009 Genuine Stella
1980 Puch moped