Lots of folks would like to do this type of job themselves. It's good that you're looking into it before you start any demolition. What you find below is what I posted to a previous individual who was interested in doing the same thing. I think you'll find it useful. There may be info on a video but I know for sure there's a good PDF presentation! Their product is good. Don't skimp by buying the 'cheap' stuff. Don't waste $$$ by buying the expensive stuff either. Find out what the thicknesses are and stay towards the higher thickness. Heck if you've got the $$$ go as high as you'd like. Here ya go ...
Go to Ashland-Davis Vinyl Products, select 'Siding Fundamentals' which is under the HOMEOWNERS Section pull-down menu labeled as 'Select a Destination!'. From there, there's a link for 'Is this job for me?'. Do check it out.
Once you're done there, go back to the main WEB page, and select 'Installation' which is under the PROFESSIONALS section pull-down menu labeled as 'Select a Destination!'. Then, you'll need Adobe Acrobat Reader to view the PDF file for Installation Instructions. (Now remember, these instructions are geared for pro's, so it's labeled ...) Believe me, if you don't start this job off right, you'll screw it up big time!
I do have a practical suggestion. Habitat For Humanity, among others, always wants people to help them build/remodel homes. Contact them to see if you can work w/them on a project. Don't just do siding! Suggest to them that you'll help with clean up and general carpentry and such but you want a guaranteed 'shot' at helping to install siding. (If HFH isn't currently operating in your area, contact them to see where they are. Maybe they know of 'brother' organizations that do the same thing in your area.) If this doesn't work, you'll have to get imaginative to find the organizations in your area that are like HFH. (Start with the Building Inspectors and the Zoning Board in town. I'm sure they can point you in the right direction.) This is a way to learn AND do some good.