My biggest fear at this point: Buying at the top of the market and only seeing losses (I've run into this in the stock market and crypto, so trying to avoid the trifecta here) 

A friend of mine who runs a large property management company likes them a lot and would have chosen them over AppFolio if he was starting his company today.

Arguably, more properties well chosen and cash flowing are safer than having one cash flowing property.

You need to have an expert work with you in your chosen market.

Not realizing that while these people may not have "Chosen" to be poor, they did look at all their housing options and decided the dump, for $300, was either a) all they could afford or b) they didn't want to spend more for something nicer for their own reasons.    

If you were in their shoes, wouldn't you wish you'd have chosen a floating rate loan and saved $2 million? 

Everyone thinks of the landlords as these rich a$$holes, but have you ever thought-- they care, and are using their resources to better not only themselves, but their chosen  investment area/community?

And another 9k in stocks, about another 1k in crypto currency.I️ was wondering if you were me , what would be the best way to put myself in a better position for the future .

Also getting practice analyzing properties in your chosen market is priceless experience as well.

It comes from having purpose and faith in your chosen path.