Is everyone else making bad investment choices or am I just being too conservative?

Just so you know - you can leave/switch brokerages pretty easily so don't worry if you make a choice and then decided to go a different route too.

If after analyzing many different properties in your area you find that it is hard to reach your goal, you have several choices.1.  

It'd help to look up the demographics of the target area and combine that information with the types of homes being sold and use all of that information to make your choice. 2.

But there are not many good choices in this seller market, either buying REO required a lot of work, or investing out-of-state.

In our experience (only 2 units, but over ten years) the worst of the worst tenants are those that made the choice to damage housing or not pay for housing when times got tough.

Deciding what I want to achieve: I want to learn a great deal more about real estate investing and continue to acquire rental property that will generate passive income, gaining financial independence, which will give me more freedom with my choice of day job in the future.  

If you are interested in being an investor as well as an agent then a Keller Williams office is probably a better choice. 

Given the cost and market I don't think the cost of stripping the brick is a choice right now and painted brick is very common in the area.

Old article, but breaks down the two choices-https://www.biggerpockets.com/renewsblog/2015/11/1...The as far as out-of-state, you can go the turnkey route or the DIY route (I have an article comparing these two too).