Search for "Recursive Make Considered Harmful". That contains examples
of how you make make really work.
                                                                                
This is a rule that's useful to put in all your makefiles:
                                                                                
%.show:
        @echo "$* = $($*)"
                                                                                
So whenever you're not sure what a variable in the makefile is getting
set to, you can do "make FOO.show" and it will show you the value of
$(FOO). This helps a lot with debugging.
                                                                                
The other thing is to produce dependency files which work; the
recursive make paper above explains this. Then you write generator
rules and everything else will just fall into place.
                                                                                
Don't be scared of creating new extensions for things, so that you can
use them to trigger off other rules. If people whinge, you can always
delete the intermediate files when they're done. But, for example, I
build yacc and lex scripts into .C_ and .H_ files. I then have a rule
which will turn .C_ into a .o by compiling it; hence .C_ means
"machine generated C++".
                                                                                
The reason for the intermediate stage is that you can't just write
generic generator rules for .C because it'll moan that it can't work
out how to check other (human written) .C are up to date - so you need
to differentiate the node types. Essentially there are three species
in well formed make ecologies. Leaf nodes, which are always human
edited. Branch nodes which a) depend on leaf nodes or branch nodes and
b) are ALWAYS machine generated. Links; which are sets of rules to
compile a number of child nodes into a parent node.
 
Note that it is no problem that the graph of these contains cycles -
however containing a loop is an error.
 
Most make problems are caused by:

1) Believing there are only two species, nodes and links.
 
2) Failing to understand the way % rules are matched. Read the guide carefully.
 
3) Failing to "debug" the makefile in the same way as you would debug
other code. Too many people don't speak the language so they're as
stuck debugging it as they would be debugging any other programming
system they don't speak.
 
4) Failing to generate dependencies properly; without telling the
system where the links are, it cannot possibly work out how to build
things properly. When in doubt OVERGENERATE dependencies. Otherwise
you will end up not building things that you should.