Think about this for a moment:
Files stored in a database: How are you going to transfer them to MySQL or another database engine later on? All blobs are not created equal between databases (nor is their support for them consistent or bug free).
Someone will have to write a script to export the data and import the data into the new database. What if they botch up the blob export? What if they botch up the blob import to the new system? Where will you find someone who will know how to code for both database engines? Are you absolutely sure you can just do a CSV file export and get all your data out without it getting mistranslated?
Now think about storing the files on the filesystem:
How will you transfer the files over to the new system? Before answering this, how many files are there? If its a boat load, then maybe by CD, tape, hard drive, you name it. Or if you have bandwidth, you could FTP the files directly from old system to the new system. Sounds pretty easy - if anything, it would just take a lot of time, but you'd know the content is all there.
But what if they don't store the files in exactly the right place? Well, somewhere you should specify the base path to where the files are currently stored. On a Windows box, it might be something like: C:/thewebfiles/gohere/ and all the files work off of that base path. On a *nix system, you'd have to change the path because they don't use C: so it might need to be something like: /thewebifiles/gohere/. Ideally, you want this stored in one place so when its time to move the files, you only need to go to one place to make the change.
Also by doing this, you add in the ability for these files to be hosted on a completely different machine within the internal network. Meaning you could design a setup where the web server talks to the outside world and also talks to a local, private network. On that network, you have a database server to handle the load, and a file server to handle all the files (it could even be one of those nifty 1U rack hard drive arrays which could hold 1 terabyte or more of data).
The flexibility you'd have could be endless depending on how you design your system.
Storing the files in the database is a bit dangerous in my opinion.
Something else to think about: What if someone blows away a row accidentally? What if someone blows away the entire database accidentally (been there, done that, not fun). If you're files are stored outside of the database, you might be able to do a few things: recover the database faster since you're not recovering a boat load of files stored in blobs, since the files still exist. You could change the web pages to access the files without using the database (this could be ugly, but if its going to take a few hours to restore the database, it might be a supper quick fix to keep customers happy).
Another thought: what if a file has a virus? If the file is in the database, will you still be able to scan it and fix it? If its stored in the filesystem, you could at least run the virus scanner on that machine on a regular basis and do house cleaning.
Again, if you're still serious about doing it in blobs in MS SQL, I HIGHLY recommend looking at MSDN (Microsoft Developers Network). There's a lot of technical notes regarding blobs and their useage (and their bugs). With MSDN, you may be able to figure out your blob problem.