Rating Self Hosted web based software for total noobs

Being a noob at something is hard, It's hard to know how much we don't know, even when we know a little bit. It's hard to be privacy minded, or want to have fun like other people with software and technology when all the coolest stuff isn't easy to comprehend, or has documentation that's difficult to parse, or takes knowledge for granted.

This blog was started because there are so many people that want to self host. The real problem is documentation that takes knowledge for granted and I want to be a perosn that puts software that's used for privacy, and self hosting to the ultimate test.

Can I (someone with very limited knowledge) get a self hosted service and server up and running? and sharing my thoughts on how difficult I find it!