I’m one of the riders who wanted my feet down on my first bike. I am not ashamed of this. It was some security and I needed it. Being able to put both of my feet down gave me confidence that I wasn’t going to tip over, wasn’t going to damage my bike, and was going to make the ride. When I found my lowered F650GS, I was ecstatic. Honestly, it’s been the perfect starter for me. It’s got a propellor on the side, I can get my feet down, and it’s Mandarin Yellow. It’s autobahn-friendly, dirt-friendly, and (grrr!) garage-friendly. And, if I didn’t mention it, I can get my feet down. With a slight bend in my knees! I spent a year and a half with it becoming a confident and reasonably capable rider. To that end, it served its purpose with distinction.
My confidence grew as I got proficient with the baby GS and I was starting to wonder what it would be like to ride a non-lowered bike. I was starting to only use my toes at stops. I was bending my knees so that my heels weren’t down. I was experimenting with not having my feet down by tripoding all the time. Due to some motor issues this summer, I made the decision to buy a second bike. The prospect of a vintage BMW floated by, but I dropped it due to not wanting two dead bikes. 
I wanted to try something sportier and smaller, but also, something that was a bit taller.
I went with a Honda CBR250R. Before I broke it in, I could sort of get my feet down, but not all the way. My heels had quite a sliver of air under them, depending on where I was on the seat. My feet came down in front of the pegs (gasp!!) when they came down at all.
Riding the CBR250R is a completely different experience from the GS, not the least of which is the fact that my legs are straight and my feet are mostly down when I am stopped. I tripod it everywhere, because both feet don’t go down on the ground like on the GS. And it is good. My increased confidence lends itself well to the higher seat and less foot contact. My improved balance makes handling the more top-heavy CBR much less of a challenge. And, frankly, having my down leg straight is really stable. Much more stable that I could have ever imagined when I started this whole riding thing. Now I understand those guys who look so cool and calm with a bike balancing against one leg, the other foot up on the peg. I can do that too now. 
Recently, though, I’d started to question my choice of the CBR, due mostly to the cost and the extent of the issues with the GS, partly due to the amount of back pain I’m enduring as I convert to the new riding position. I got the GS back on the road last night, and I now have a different perspective on the matter.
After riding the GS last night, I know that the CBR was not only the right decision, it was a good one and a very good one at that. Just as wonderfully good as the yellow GS has been. The CBR is teaching me confidence in a different way than the GS did. And honestly, the stupid GS pretty much rides itself. You tip it into a turn, it pops right back up. It’s so stable. The CBR wants to lean and lean and lean. Just going right to my dream bike, a 1983 R65, would not have given me a new view of riding like the CBR is giving me. I also wonder if starting low gave me a edge up on the going taller game – basically, I have something to compare taller to. I can from the get-go understand why the taller CBR is just fine and in some ways even more stable at a stop than my low GS. I can appreciate the CBR more because I know what it is not. Also, did I mention the GS is low. Like too low. What do I do with my legs low. I still love it, but now I think it needs a lift kit – I’ll find someone in the US to swap regular parts over for my short parts when I get home so I can put down a straight leg instead of a bent one and get some of that newfound stability.
I think that I can serve as the poster girl for starting with a lower bike and moving up. The low GS gave me the tool I needed at the time. It’s still a fantastic tool that I adore riding. But I didn’t stop there. I moved a bit higher, and I can now see an F800GS in my future. The seat height no longer scares me. I might not be seeing that if I was still fighting with a taller bike from day one. Just like your first bike doesn’t have to be your last one, it also doesn’t have to be te tallest one you ever ride. You can always move on up with the next one.
The answer to getting your feet down is do it if you need or want to, but stay open the idea that one day, you might find yourself pretty comfortable up in the air, sticking a toe out once in a while to touch down. It worked for me.
note – It was pointed out to me that the CBR is very light, and that is helping with the transtion. Yes. And there will be more transitions in the future, thanks to that.