Alex,
We allocate as many 2GB-maximum files as we anticipate necessary to accommodate the data for a tablespace. So if we anticipate needing (eventually) 40GB for an application, we allocate 20 autoextending 2GB-maximum files (which translate to 200MB initial allocation...20 10MB-initial files).
And, hey, if you have a good business/IT reason for doing it differently, then, by all means, go for it. I was just asserting a method to avoid horrendous pre-allocations of disk space that may NEVER get used if there was a mistake on initial estimates. Remember, it is not fun to try and whittle DOWN the size of a file once it's allocated.
And, no, we don't check free space on a daily basis; we run an automated report on Saturday nights that checks, and if we're within 20% of our file maximums for a tablespace, we add another 10mb, autoextending, 2GB-maximum datafile. So we manage it by exception.
Cheers,
Dave