@Jamie Kammers maybe try to think of your fears from a different angle. You mentioned you passed a few deals because you were worried or afraid. Part of that fear I'm sure is a fear of your analysis being wrong and you wind up losing money, which is a reasonable fear. For me though, I'm afraid of missing a good opportunity. Now, obviously I don't mean go after everything that looks even half way decent. I just mean you should be more afraid of not jumping in when you find a great deal than of the deal itself. Most investors tend to lose a little on their first deal due to inexperience, but a few things I've either learned personally or through someone who has been there.
1. When you analyze, look at expected numbers and worst case numbers. That way you're in a better situation should things go south, and if things are better than expected you have a nice little bonus.
2. Base hits win a baseball game, not home runs.
3. Real estate is a rather forgiving investment compared to other vehicles. Let's say your numbers come back when all is said and done and you're cashflowing negative $50. Rents raise every year which means that property will eventually cash flow, and might even cash flow big with the upcoming recession/depression we're probably going to see. Also depends on the market your buying in.
4. After you get the first one out of the way, future deals become easier. Again, don't just jump into something for the sake of jumping. Make sure it hits the numbers you want.
5. If you're doing any sort of rehab, make sure your first one is an easier rehab and not a full gut rehab.
6. Never stop learning. My friend said it best about real estate investing, "You either pay to learn through personal experience or through education." I make it a daily habit to either read, listen to a book, or listen to a podcast for at least an hour.
7. Don't be afraid to ask for help. My wife and I finished our first BRRRR about 2 months ago and already jumping into our second one. With both of them, we reached out to my mentor and other investors to get more eyes on our numbers. BiggerPockets is an awesome community, you can always make a post here if you want more pairs of eyes looking over your numbers.
Hope this helps!