Here is a shot of my bike with a 21 front, stock size rear and stock height in the front with 13" rear shocks.

 

21/16 here on an '08. I didn't lower the front and the only negatives are that I needed to shim the kickstand so it wouldn't lean so far, and backing the bike up is a little harder on soft ground- maybe because of reduced leg reach or maybe geometry, not sure why.
I've been riding with my stock 16 up front for a few weeks while getting my 21" wheel worked on and I really don't like the ride this way. Scraping boards and I feel like I'm being pushed forward.

 

I used to have a 18 rear 19 front. I switched to a 16 rear and 21 front with legend suspension. I wanted my bike to sit very low when all the air was out I lowered the front suspension with progressive mono shock 1 inch. Drop.

 

I see no need to shim the kickstand with a 21" front wheel. I have never actually even thought about that.

 

Thanks guys great info.Hogpro can I safely run a 190 or even a 200 rear Tire on my stock 16 enforcer wheel off a 2014 street glide? Also take a look at the picture of my bikes front fender 19 enforcer wheel,you think i should drill out the rear fender mount 3/8 drillbit to tilt fender forward just a hair? Thanks for the help!

 

I have a 21 front and 18 rear on my 2008 Electra Glide. did not change anything thing suspension wise. rides like a champ. does sit higher however

 

Nice looking bike! I like my bike low, good news for you is you'll never scrape and I bet you could carve it up in the twisties.

 

On a 14 you need brackets to raise the stock front fender for a 21" wheel. If you can find a 200mm 16" tire it will probably fit. In all honesty I sell very few 16x5.5 rear wheels and when i do I always put a 180 tire on it. On a 17x6.25 you can do a 200 tire.

 

Thanks for the help, much appreciated!

 

My pleasure. There are a lot of different things to know about wheels and thankfully we know the answers to some of those questions. Here is teh page taht has the brackets on it. Scroll down a bit. You'll see them. http://www.hogpro.com/showcat2.php?catid=26