Vinyl siding

Anyone on here have experience with installing vinyl siding? the house i'm buying has a HUGE 2 floor 2 car garage. its ancient and the original owner really didnt maintain it except for the roof. its wood siding, and id say 60-70% of the wood is getting bad. some portions need to be outright replaced. can i add vinyl siding right over the wood? i think portions of the wood can still be tacked into, the really bad pieces i would obviously patch with something and replace. i'm sure something would need to be installed over the wood first, some sort of a barrier for weather proofing? excuse the noobness, this is my first home and i have all kinds of ideas floating around in my head lol. i have a picture of the garage i can upload later. as part of the FHA loan requirements, i had to scrape all of the flaking paint off and repaint the whole thing before they will let me close on it.

 

did i read that right.... "2 floor 2 car garage"??

<caveat>...first of all, i'm not anywhere near an expert or guru on siding</caveat>

...i know when the siding was replaced on my home, the original vinyl siding was nailed to wood sheathing, ...there was no moisture barrier, at least not between the sheathing and the siding, ...but when it was replaced, i had them put some "house wrap" type barrier between the sheathing and the new siding... i don't know if that's a code requirement in your area, ...don't think it was for me, but figured that was the right time to get it...

 

I would definitely install a housewrap first , vinyl siding is notoriously leaky , which is one reason I hate it

 

yep, but it is basically zero maintenance... never need to paint it, which i like

 

ooops, forgot to upload the picture. i'm relatively handy, so i may like to attempt this with a few friends (2 of which are in construction so i think we;ll manage lol). i just wanted to get a good grasp on what all is involved and what i would need so i can start getting materials slowly but surely.

here is the garage at the 95% completion of painting. you can really see the difference between what was painted and was not painted. the homeowner said he never really did anything with the garage in the 15 years he lived there wth the exception of a new roof 2 years ago...which may explain why the wood siding was so bad.

 

after doing some research, i'm not sure if i can put siding directly over the current material. which sucks, because i really really do not want to have to take down the current siding. anyone know if i can side over top of this? it has the flat corner pieces i could anchor into and sort of bridge over top of the current siding, but i'm sure i would need something in the middle to also anchor to maybe?