Whew - lots of questions, but good ones!!
1st - I don't like parking lots or roadways much!! Too rough on my kites!! You'll wear out your leading edge or the tips where the leading edge ends!! Grass is much better!! Indoors, any place seems to be ok, I use an indoor soccer field when empty!!
2nd - Recommended kites! That's a loaded question, everyone has their own "wants" from what they use!! I would suggest 2 kites - one for indoors and one out!!
a - an iFlite for indoors! Small for living rooms and kitchens, but also comfortable in larger spaces!! Available through Windswept Kites! Cost is only $32.00 delivered to your mailbox!! Internet store that has a ph# on the website to talk with Rob Banks in person!! Works too, so he calls back as he has time!! Service was excellent from him!!
b - Outdoors is a little more tricky! Lots of great choices here!! The Zero-G, Skate, Wala, Horvath's Hybrids, etc!!! The Zero-G and Skate and Wala are offered through Into the Wind, a store out of Boulder, Colorado!! They have a catalog you can get and drool over!! I really think the Wala is a good first choice, can be used in or out (it has instructions included for the changes needed), is really well built to take any abuse, and ready to fly with line included!!
PS: I know where you're coming from, I've been through a stroke, 2 heart attacks, both hips replaced!! So this glider thing has me hooked big time!! There's lots of choices out there, pick wisely and enjoy!! If you have more questions, feel free to ask!!