Well, 200 pix at 5MB each is 1 gig. You'll pretty much need your own internet source to do that since I would imagine the upload speed of free Wi-Fi is going to be pretty slow and would take a very long time. You could do a few at a time I suppose.
And I don't know what you mean by "many times". You want to upload the same folder many times?
You'll need to check on the storage capacity of each site depending on if you want free or if you're going to pay for storage.
If you're archiving .jpg's then they're already compressed so zipping them won't do much.