Roofing It...

Was wondering if anyone has replaced their own roof? My husband is very reluctant to try this, and we need a new roof very soon. Of course our money is very tight.

If replacing it ourselves is out of the question, what are realistic estimates for the cost of a new roof? Our roof sits atop two floors, and measures out close to ~1,650 sq ft. We live in KY- hot, humid summers, temperate winters. Lots of damned rain normally (which is why we need to replace the roof- it keeps leaking when it rains and is very old).

Reddit, do you have any advice? We'd heartily appreciate it. Thanks for the support! Pun intended.