I haven't had a chance to read all the other responses so sorry if any advice/suggestions I provide are redundant.
I was (still am) in similar shoes as you are currently. I studied my butt off, listened to any podcast that was relevant to what I believe my niche was and read any book related to it as well. After 4-5 months of self-induced education and underwriting/analyzing multiple deals, I finally jumped on my first apartment (duplex). How'd I know it was a good deal? Well after underwriting so many deals you are really able to differentiate a good deal from the numerous bad ones. Once you see one that makes any logical sense, you pounce on it (after further review of course; Also, I heavily utilized friends/acquaintances that were also investors to get their take on the said property I was interested in. Always best to have multiple eyes looking at it).
I'd be happy to share more details on this if you like, however, I do not want to self-indulge.
Anyways, to your questions, I would suggest doing your first one on your own. Why? You are clearly well rehearsed in self-education, so consider this "first deal" as your first exam. If you do well on it, then you know all the months of studying you did were beneficial and worth it. Now if you do poorly, then you take it as a learning lesson and persevere through, sure it will suck to do poorly, but nearly every good investor, business person, etc have failed once or twice. Look at Michael Jordan, considered one of the worlds best basketball players in the world, here is his quote on failure: "I've missed more than 9000 shots in my career. I've lost almost 300 games. 26 times, I've been trusted to take the game-winning shot and missed. I've failed over and over and over again in my life. And that is why I succeed."
As far as your capital goes, I personally would leverage it out between several different properties. That is why I believe real estate is so great, you cant really do that too much anywhere (I think, hah). Buying one nice property will surely cash flow, but then you're just stuck sitting around, waiting for your capital to generate. That is sort of where I am at, however, my intention was to house-hack, so I bought a bit over my means to move into a place that "was move in" ready to eliminate my living expense.
Hope this helped!