Start with the end in mind.
If you want long term rentals, which is sounds like you do, don't bother learning how to flip. The risks are different, the taxes are different, the requirements of skills are different, and in the end you won't have a cash flowing asset like you want.
The rest of your question comes down to how much risk you want to take on. For my first deal I went with a depressed asset and did a big rehab and it paid off huge. That's not saying you should do that, just saying it worked for me so it certainly could work for you.
Taking risks, skin in the game, is how you learn. I say go get something pretty close to your ideal goal project and get through it. It's easy to put the first deal on a pedestal but the reality is if you want to do this long term it's just going to be one deal of hundreds, it can't make or break you. Think of it more like paid college, even if you come out at a loss in capital you make a giant gain in experience, good trade. Odds are though, you'll make money and get the experience ;)