I can imagine what your launch might feel like. My sister-in-law lives on the top floor of a 30 story building, adjacent to Millennium Park in Chicago. She has line of sight to Navy Pier, only a few blocks to the east and much of the park to the south. I've been flying since late June and haven't yet developed the courage to launch off of her roof.
As far as identifying front from the back of your drone, I STRONGLY recommend colored strobes (and a white one). Velcro is your friend as it gives you mounting options. Initially I got the clear strobe with the "headlight" mount (purchased unmounted). But as I got more courage to send it further and higher I wanted the clear strobe on the bottom and then purchased the red and green strobes. If all you're looking for is orientation the clear headlight is really good. You may also see that I have the red and green strobes attached with elastic bands, the idea which I ripped off from someone on YouTube. All my strobes were purchased from Firehouse Technologies. Here is their 4 light kit, which is the best value (and wish that I had purchased it in a bundle).
Firehouse 4 light strobe kit
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