funny you say that because as i hee'd and haw'd on doing it myself I thought, I would be happy to give it a go myself...if it wasn't my only mode of transportation and i don't have a partner or a bud who can get me around if i ran into a problem that i needed something else to resolve..tool or time. i believe in my 57 years of living the projects i didn't get into trouble on were those that i was absolutely confident i could do after researching. then there's those that i ended up generally spending more money & time on to backtrack and fix. basically, through some painful experiences i've learned its best to respect my limitations. lol.
first time i shingled a house was quite the story. i had done small sheds with a simple roof, but my last house that i decided to do myself after nights of research was almost a disaster. first, it had cedar shakes. those were ******* to get off the roof. they don't just shovel off like shingles. then, it had all kinds of valleys. more tricky than your average roof. then finally, it was the roof on a 3600 square foot house. it seemed to go on for miles and miles. felt like i'd never get it done. but saving over 12K in labour was too much of a temptation to ignore. and i have a touchy back too. and then there was the heat on that roof in July. that project damn near killed me.