Things I never entered into a contract to have done......seems like a scary way to do business and from what I have read there is lots of risk for the potential buyer too.

Very high risk and far from dependable.In your position I would be looking to flip homes for the next ten years.

That person is either very knowledgeable or taking a huge risk. 

Also, be very open to your investors about the risks and expectations for the property -  communication up front and throughout the project is critical!

I don't think there's a right answer but you need to know what you are doing.When you take multiple applications at the same time and then pick the "best" from the pile, you run a real risk of a discrimination complaint.

I use a scoring system that helps me get the top application identified, and I concentrate on that one until they prove themselves out or not.My applicants gain points for holding the job for a year or more, lose points if they have held it 3 months or less, gain points for having lived in the community for five years (to me low risk is they have been commuting, but moving to commute often backfires in my area), etc. 

I just closed on my second rental property 2 weeks ago and am now looking to save for my next investment.I have $5,000 I’m willing to take a little risk with and have heard good things about Fundrise and RealtyShares. 

If I do want to put myself in that place, and I did when I was younger, am I willing to shoulder the risk that comes with doing so?

I've always had issues with tenants paying rent late, so i decided to take risk. 

We didn't look at condos recently because of the high fees and risk involved but we do own condos in Wisconsin that do well.