Siding and gutters are exterior projects that require some degree of skill and experience. The tools used for both overlap, aren't cheap and can be bought at the BORG (Big Old Retail Giant).
A lot of care needs to be taken when installing siding. Siding can look fine and still be very wrong. If improperly done your house rots away a little each day or grows mold inside the walls.
The picture to the right shows how not to do a siding installation. There is a lack of proper preparation and tools. The wood structure of the house should be protected by felt paper or house wrap because all siding is going to allow some moisture to get in even if you do every thing correctly. Even a tiny amount of moisture over a long period of time will cause problems. Yet your "budget" builders and remodelers do this stuff every day of the week.
Installing siding from ladders is amateur hour. Jacks or scaffolding should be used so that you and the siding are safe. Save a bundle and get a quality job when you do your own.