I have wanted a Harley for a long time now but now that I have this savage I don't think I really need one.  The savage sems to be perfect for my 5'6" hobbit body type.  This is more than enough bike to whip me around.  But sometimes I just want a big growling vtwin and a bigger gas tank for more mileage.  I am still about a year from being able to afford a bigger bike but that doesn't stop me from looking a good hour or so a day, lol.

Did you move up to a bigger bike?  What did you get and how was the change? What convinced you to get a bigger bike?  What do you want to "upgrade" to?  Is a fuel injected bike a good idea?

If you are doing a lot of Hiway miles ( long trips) and /or two up consider a bigger bike. I moved up to a c50  last yr. it is more comfortable on the long haul. The wife is now going with me more and more and the c50 is much better for two up. I now have a c90 which is way more powerful and roomy. At 70 mph it feels like it's only idling.

As always there are trade offs. You will have to decide if  loosing the maneuverability and lightness would be worth it. If I was just tooling around town and doing short hiway hops I would have stayed with the s40.

The S40 is perfect for what it is. I've had smaller bikes and bigger bikes. I've had other thumpers, parallel twins, V-twins, opposed twins, four cylinders, chain drive, belt drive, shaft drive, four stroke, and two strokes. They are all great! Big bikes are nice for longer distance, weather protection, bringing the S.O., packing a weeks worth of gear, etc...
The smaller ones can be way too much fun through the twisties and still take you hundreds of miles in a day. There are no bad bikes.

But to answer your question: Buy the bike that you want. Don't worry about what anyone else thinks of your bike. If a 50cc scooter thrills you, buy it! (I did.) If a big sport touring bike sounds like the way to see that far off place, go for it! But if a fun little bike with soul stirs you...keep the S40. Mine will be in the garage until the next bike shows up. (It may stay if there is room for three motorcycles and all the other junk out there!)
I better shut up now. (I get too wound up over bikes... )

I am in a similar dillema as you. About 15 years ago, I really started to get the itch for a HD and seriously considered a few options, but as a young newly wed couple, kids started to arrive and the dream of a bike slid further and further onto the back burner. Finally after 5 kids I conviced my wife that I still wanted a bike and she had no interest in riding with me at all, so the S40 sounded like a good option. I've had the bike for just over 2 years and this year was the first time she ever rode with me on the bike. Needless to say, after 1 ride was another ride and now she wants to ride with me more often, but complains about the passenger seat and how cramped we are when we are both on the S40. She has even asked me a few different times what it would cost to get a bigger bike that would work better for the two of us to ride together. I've always had my eye on a HD Road King, and for 2up I think it might be the ticket, but I have a hard time thinking about forking over that amount of $$$ so I've started reconsidering bikes like the C50 and C90 but no matter what I find, I still plan on keeping the S40 for around town and so that she will have a more manageable bike for when she decides that she wants to drive one too  

How does a sportster compare to a S40?  Is an 883 about as fast as our savages?  I assume a 1200 is significantly faster at least top end wise.

I like the sound of a Harley... and the look, of the engine, at least...
They do get excellent gas mileage for a big bike, (better than ours at 70+mph)...
... but,... the controls... shifting, clutching, kickstand,... are caveman.... and too much vibration,... .
.. and reliability,... Hog riders consider engine rebuilds to be routine maintenance...

If you want a good Harley...  ...buy a Japanese one.... ...


Personally,...  I want ten more horses, and twenty less pounds...
(I'm at 34hp and 320 + 140lbs right now)...
10lbs per horsie... = Bouhyahhh!...
Zoom, zoom!... ...

Victorys are sweet. They are on my wish list,

The s40 is just a fun, flickable and simple bike. A more comfy seat( perhaps an air hawk), forward controls and exhaust will just enhance the experience that much more.

My Vulcan 800A is also a fun, comfy bike, sorta like a big bother to my s40. Isn't as flickable, but still handles nice once under way. I love the easy turning and posture of the tall, skinny front wheels.

I'm havin' a ton of fun putting in some quality wrench time on my Savage, which is kinda why I bought it in the first place.  I wanted a simple bike to hone my mechanical skills on, and the LS650 is about as simple as they come.  I can only really justify the cost if I do all the labor myself, and I hope to be one of those dudes that can strip and rebuild the whole thing with only the tools in their toolbag.  A lofty goal, I know...

That said, when I feel comfortable enough with my skills to get into something a little deeper, I'm gonna try and round up one of 2 bikes; a '75 Shovelhead or a '75 CB750.  I was born in 1975, so I wanna roll something made that year too.  I'll still keep the Sav if at all possible.  Loves me my little thump.