Welcome to MDC Jenns! I'm sorry you've been having a frustrating time TTC, but you have found a great place to get advice and support. Instead of asking questions within this thread you can feel free to start your own thread with your specific questions (so you'll get more responses specific to your needs) or join the group threads for those TTC based on age group or stage in their journey (waiting to O, 2ww, etc.). Those are like chit chat threads where you can check in, ask questions, and offer support to others as well. Here's a wiki to help you with the acronyms that you'll see around here: http://www.mothering.com/articles/abbreviations-and-acronyms
I personally do not have experience with progesterone supplements or clomid, but many others here do. I wanted to say, though, that even if you ovulate, low progesterone can cause issues with your luteal phase making it difficult to sustatin a pregnancy. I also wanted to note that even if you bleed, it does not necessarily mean that you ovulated. Women who have ovulation issues often do bleed, but it's not a true period if it has not be preceded by ovulation. This type of bleeding is hormonal in nature and usually referred to as breakthrough bleeding- it happens when the lining has become quite thick and starts to shed on it's own regardless of ovulation. To confirm ovulation I would highly, highly recommend starting to chart your basal body temperature and your cervical fluid. OPK's can't confirm O either- they an only tell you when you're gearing up to O, but not whether your body succeeded or not. Plus OPK's are not always the most reliable things for all women. If you'd like more information about OPK's, charting, etc. just start a new thread! Good luck!