If you have not at least skimmed through fast.ai, you should definitely do that, as the course itself addresses some of this and the people on their forums are

If you have not at least skimmed through fast.ai, you should definitely do that, as the course itself addresses some of this and the people on their forums are among the most helpful I have ever seen! Second, this could be more than enough! Especially if you are doing transfer learning. Third, you can "inflate" the amount of images you have now with "Image Data Augmentation"