Hi @Clayton J. and welcome to BP. To help answer your questions, here are my thoughts:
1. If you have the cash or investor partner to do a flip first, that's great. Family/friends may be able to provide funding for a flip. Otherwise, the buy and hold is a great way to increase cash flow and save up for a flip.
2. My husband is very handy and likes to care of things himself to save money. However, as @Chris Pastrana pointed out, it is often faster to higher someone done just because you won't be always be available to get it done in a timely manner. If you want to learn, one suggestion to get started is to go to Home Depot. They always have classes on diffferent DIY projects and if they don't have one on what you want, just ask. They have always been very helpful to me in understanding how to do some of the smaller projects on our rentals.
3. I think this is a good idea. My husband is thinking of doing the same thing even though he is fairly good at being able to identify problems already. In my opinion, education is never a bad thing.
4. The first place to look for a mentor is usually your local REI as @J Martin suggested. You might also be able to connect with someone here who can help you out. In the meantime, you can always ask any question you have on the forums and there is always someone who can help with an answer.
Another helpful tip is for you to upload a picture. It helps people identify and connect with you better.
Best of Luck!