so I bought my 07 Heritage this past Nov. always wanted one and just always liked the old school type look of them.
But now I find myself more and more looking and liking the Street Glides. not sure why but my opinions of them have changed a lot as far as looks go.
My wife rides with me quite a bit and loves to ride as much as I do and now that I keep kinda talking about the Street Glides more and more shes thinking im a moron (prob am) because we just bought this Heritage.

how much of a difference is there in the Heritage to the Street Glide as far as riding, comfort and so on.
I have found a sweet 08 Street Glide for 10k that has like 36k miles on it and all silver....not that im looking or anything

 

Not sure, but your cool factor will go up about 90 points.

 

NIGHT AND DAY! Last year I went from a Fat Boy to a Street Glide. Completely different bike in every way...I find it way more comfortable then my last two softails. You feel the extra weight of it but, it's just a way better road bike. I do mostly highway running since I'm out in a sorta rural area.

 

Go to a Dealer and test ride one, and answer the Question yourself.

 

I have an 07 Heritage and a 13 Streetglide. I love my Heritage, but when it comes to any sort of distance riding (over 75 miles) I take the streetglide, and if its out of town two up we take the Streetglide. Its just a more comfortable bike, and it's more functional for me, especially now that I have the tour pack on it.

If you are serious about getting a Streetglide, go with an 09 or newer.

 

I went from an ol' (2000) Road King to a Rushmore Street Glide early this year. Not as much difference as from a Softail to conventional swing arm I don't reckon, but without a doubt, a much better ride. Not 100% positive, but I don't think the Heritage has air shocks. If that's true, that's a huge difference in comfort and versatility. My '14 SG had 24+K on the clock and cost me $12K even. I got real lucky. Most used Rushmores are in the $15K to $17K range, which I would've never bought just because I didn't have the cash. Still, I was willing to wait for the right price on a Rushmore if I had to. 36K miles on an '08 for $10K seems a bit overpriced to me. Look every day and be the first to reply to new ads for a '14 or above, and I bet you can find a much better deal than that. Also, be willing to travel to get it. I had to go to Jacksonville, FL to get mine, a bit over 500 miles round trip. Either way though, I'm pretty sure you'll feel a much-improved ride with an older SG over your Heritage. As is always the case though, YMMV.

Blues

 

Better yet, rent one for a day and ride the snot out of it. Then you'll know for sure. A test ride isn't enough for a major purchase IMO

Then BEFORE you buy make sure you get an insurance quote - you don't want a 2X increase in insurance to surprise you.

 

Why 09 or newer just curious?

 

It's around $149 from Eagle Rider, you get a 10% discount if you are a HOG member. Rent it for a day or two, let the wife ride on the back and see what she thinks.

Tell her you are doing it for her comfort.

 

I did this with a 2013 Electra Glide Classic a few years back. It was nice, but I didn't care for it. Too top heavy and it sat too high, so it was hard for the wife to get on and off. The hard bags offered no advantage to what I can carry on the Softail with leather bags and a TBag. Wife says "I like the softail a lot better", and you know how that goes, happy wife happy life. $150 spent on a rental saved me $16,000.