I have an 06 SG, am 5'6" woman with 29" inseam. I put on the Road6 lowering bones (1"), which helped, then I did the HD front lowering kit (1") - which also helped. The bike also had a Road King seat on it when I bought it - which is narrower than the SG seat.

 

You might also want to try boots with a thick heel, they'll help.

 

Your on the right track asking for advice. You shouldn't ride when your high.

 

Have you ever thought of trying to learn how to balance your bike? Is it really that important to be flat footed for both feet? How about leaning on to one side and trying to get one foot flat footed. The reason I'm saying this is that I have never been able to flat foot any bike that I have own. I'm able to balance my bike in a safe manner

I grew to accustomed to at least getting one foot on the ground in a stable manner. I'm 5'5" so I'm not tall and I am able to ride a stock streetglide and a stock roadglide ultra with no problems. It's just a matter of balance and practice.

I don't believe in lowering suspensions except upgrading them. Stop wasting your money and get use to your bikes characteristics and how the weight of your bike is distributed. Your technique and confindence might be off.

What I do when I make a stop, is that I either lean to my left or my right depending on the road conditions. If the right side of the road is steep then I use my left foot and vice versa. If you get your balance right you can quickly center the bike and safetly put it into gear.

Keep practicing

 

Nobody has mentioned this but your issue could be easily solved with the right seat. The stock '06 seat was designed by a sadist and was the first thing to go away on my '06 Streeter.
Some seats are much narrower at the front allowing you to more easily reach the ground flat-footed. Mustang and C&C come to mind and there are others as well.
Check this out - I bet you'll find one that'll work for you.

 

This is why I mentioned contacting Mean City Cycles; they can narrow the seat, adjust the riding position, and use better/more comfortable materials for about $100.

 

Sorry, didn't know your ego was so fragile. Didn't I also mention there were others?
MCC most likely does great work and has a great rep on this forum. But custom fitting a seat is best left to a shop that is close enough to make a personal visit to. Kinda like buying a mail-order "custom tailored" suit. Sure you might get lucky but what are the chances?

 

Sure fire method to drop the bike! Add the front brake and it's all but over!!

 

Start watching some of the guys on the sport bikes, see what they do... Lots of balancing going on there with a lot of them. I see a lot of short guys on TaLL bikes and they're holding themselves up with the tips of their toes. Frankly it amazes me and so many look perfectly comfortable doing it. B-A-L-A-N-C-E

 

I had the same problem. I have a 30 inch inseam and went from a heritage to a 2010 street glide. When I got the bike I could bearley reach the ground (tip toe). I lowered the front an inch with the harley lowering kit. I sent my shocks to bitchinbaggers and they reworked my rear shocks to 11.5". I also put on a street glide screamin eagle seat. I am now flat foot and could not be happier