Is it a bad idea to compile Samba from source for Mac?
Honestly, it’s a mixed bag. I worked for a client in an enterprise environment—300+ users—with mixed Windows and Mac OS X clients and the SMB/CIFS issues were maddening to say the least. The only “solution” to some specific file sharing issues we could practically implement was to deploy Synology rack-mounted NAS enclosures and use those in lieu of core Windows server-based file sharing since those Linux-based devices handled SMB and AFP connections on Mac and Windows clients beautifully; never an issue.

But I left before any real solution was implemented for the core Windows server-based issues they faced. One idea we seriously looked into was upgrading the default install of Samba on the Mac OS X client side via SMBUp. As the developer’s page states:


  Did you lose your shared folders with the update of Mac OS X from Snow
  Leopard to Lion? You can’t see your shared folders from your DVR or
  Mediacenter box hooked in your TV? The internet tells you to install
  gigabytes of developer tools and use tons of command-line instructions
  to regain the ability to see your mac from your other devices in the
  house after moving to Lion or Mountain Lion? We might be able to help.
  
  SMBUp (current version: 1.4.1) re-instates Samba as a service of your
  mac and provides a simple interface to manage the service. Compatible
  with OS X Lion and above.


That said, I still see a “fix” like this as a “caveat emptor” endeavor. Apple really mucks around with Samba with each new Mac OS X install. So who knows what will happen if you—for example—install SMBUp and then run an Apple update that somehow conflicts with it. I’d honestly be walking on eggshells with each new Mac OS X upgrade/patch if I went down this path.

That said, the nice thing about SMBUp is that the developer is clearly devoted to providing simple/non-sysadmin level advice in the usage of this package to help people going nuts of SMB issues in Mac OS X. In fact, as the developer explains here on a “Mac OS X Hints” page on installing SMB support from source:


  I made SMBUp to help people avoid having to install XCode and
  MacPorts, both of which I love but which are overkill for something
  like this. I kept waiting for someone to come up with a simple
  installer for Samba binaries (my money was on Liyanage, who'd made
  similar things in the past) but after a year I just gave up and made
  SMBUp.


So you could do worse if you attempt to do this yourself; at least this developer is doing the “heavy lifting” for you in this case. But like I said, I would still be wary of interactions with core Mac OS X functionality with each Mac OS X upgrade/update. Thus is the reality of Apple’s odd devotion to pushing everything into “the cloud”; basic functionality like file sharing is not seen as a priority anymore.