My friend has HD everything and pays about $100 a month. Is it technically feasible for him to start renting an extra HD convertor box for $5 a month and then install it at my house that is several miles away?

Since we're speaking purely on technical terms of whether this is feasible, I'd say no it's not. Hardwiring is definitely out of the question because, it would be too expensive to run a cable that distance. It's also too far away to do anything wirelessly. I doubt there's any way to run a feed through the internet to your house. How would you control the set top box at the other location?

Disclaimer: Doing something like this would be considered stealing and I've seen some pretty harsh punishment handed down for cable theft and satellite theft.

Technically feasible? I have no idea. Legally feasible? Definitely not. What you propose is called "theft of service." If that phrase makes it sound illegal, there's a good reason -- it is.

This is hack talk, and we cordially invite you to take it elsewhere. We can't condone it in any form here.

I'm not really sure how it is theft of service if the box is paid for. I also didn't feel the need to mention that I did not intend to run a wire several miles long. I also have cable service, but I only have the Basic Service (channel 99 analog).