To do it safely its a niche and one needs to be aware of all the things that can trap you and cause you a negative experience..

I found some of my properties early on were break even or some months negative.

This creates a negative initial position.

Comes up negative?

Every positive I brought up he had a negative rebuttal.

Keep in mind, if there is enough depreciation (IRA can't take the bonus depreciation, need to use standard depreciation schedule), that depreciation might negate any positive income.

Rarely if ever are the negatives brought up. 

(From what I hear the first property can be very impactful to jump starting one’s real estate journey (or very very negatively impact it,).

Maybe I was lucky that I have started investing before information became ubiquitous on the internet.The biggest fear (being cash flow negative) is not even a real threat, because it is manageable and it will fix itself over time.

Whats funny is 20 years ago my net worth was negative and I would eat out all the time, now I have a few bucks in my pocket and I cannot remember the last time we went out to eat that was not a special occassion. :) .