Here's a recent photo of my Fatboy Lo. The larger photo also has smaller photo inserts showing some of the installed option parts, i.e., flush fuel cap / gauge, timing cover, primary cover, derby cover, levers, grips, brake / turn signal lenses (smoked / LEDs), exhaust, air cleaner, windshield, saddlebags, and so on. I plan to change the horn cover as soon as "it" is made as well.
Here's a pic of my 92 Fatty lowered. I have the same EVO fender as you do (curve comes up adjacent to the strut). I think I only got it lowered about 1 or 1.5 inches. I used some lowering bolts that I got off ebay. Not as low as I wanted, but a lot better than stock in my opinion. Go for it!!!
No. If I would have slammed the rear then I would have probably lowered the front. However, I just wanted to get rid of the rear sticking up so high. I think it looks better lowered a few inches in the back compared to the front no matter what height you are at. My two cents.