1. Yes, that should work. The search path starts off by looking for the imported module in the current directory, followed by a list of other python directories. The search order is determined by the variable sys.path.
Of course, the modules you have in your directory may import other modules in turn, so make sure that all the required ones are present.
2. Some restrictions may popup due to the environment that the program is running under (i.e.) Apache. The webserver may run under an unprivileged user, so you may not be able to create files or directories since you don't have the permissions to do so. The webserver may also be running chrooted, which means you may not be able to access certain command line utilities and such. All this depends on the webserver setup.