My specific situation
Property management web site where users can upload photos and lease documents. For every apartment unit, there might be 4 ph
Definitely store your images on the filesystem. One concern that folks don't consider enough when considering these types of things is bloat; cramming images as binary blobs into your database is a really quick way to bloat your DB way up. With a large database comes higher hardware requirements, more difficult replication and backup requirements, etc. Sticking your images on a filesystem means you can back them up / replicate them with many existing tools easily and simply. Storage space is far easier to increase on filesystem than in database, as well.