James,
I have cared for my M-B for almost 40 years. I have almost always found the cars fairly straight forward to care for. That said, some have found M-B difficult. The question is how adept your "at home family mechanic" is at adapting to different problems and situations. I clever person can usually figure things out or decide where to look for answers.
I do take my cars to the dealer for some things. Certain electronic problems need tools that I find too expensive considering how few times I might need them. I also use the dealer for alignments.
I have always purchased the manuals. For my W202's I have the factory CD, Part No. P-2700-202-06. The CD can have issues if you have Vista or later versions of Adobe. There is another option that I understand is very well done - Bentley Publishers has a new W202 manual. The price for both is similar. Here is a link:
http://www.bentleypublishers.com/mer...1994-2000.html
I hope this helps.