Any engine works best if it's textures (wich is what a spray is essentially) is a power of of 2. (binary and all that mumbo jumbo) that's why you'll always see textures come in forms like: 64x64 128x128 256x256 512x512 and these days even 1024x1024 is occasionally used in game.
Any file can be converted to a TGA with a half decent image editing program. I'm sure there are even webapplications wich can change your jpg to tga.
Not sure how source works but on the old half life engine you needed atleast 1 pure blue pixel to get any type of transparancy so keep that in mind.
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