You can tie multiple properties and activities together to meet this test, but that alone won't necessarily allow you to turn passive losses into active, it merely changes the presumption that they are passive2nd bar:  You have to show you are actively engaged in rental activity/property management for at least 500 hours in the year.

The ADA defines an “employer” as any person who is: Engaged in an industry affecting commerce;Employs 15 or more full-time employees each work day;For at least 20 or more calendar weeks in the year.

I’m close enough to retirement age that I could make this my primary occupation within a few years and, with a little luck, invest on my own - but I like the idea of also investing other people’s money as a way to help grow their capital alongside my own.I’m fairly early on in my research but I am stuck on what seems a straight-forward tax problem.

It might benefit you to engage someone that understands real estate investing to be able to take advantage of these discounts, as well as use them to double check your work until to you grow to a point where it makes sense to outsource.

I'm also hoping for the opportunity to help out fellow investors so I can gain some of their insight and learn along side them as they develop their portfolios.

There is a program referred to as a Rollover as Business Startup that allows you to use existing tax-deferred retirement savings to capitalize a business that you are actively engaged in. 

@Bruce Harding if neither you nor the seller are experienced with this type of property I would recommend you both consider the value of engaging an experienced agent to represent your own respective interests.

My step dad has been working closely for the past two years with his landlord alongside her other friends remodeling homes.

Go grab your signs and throw them away.Of, if you're willing to engage in criminal activities to make a buck, look for more profitable opportunities than bandit signs and wholesaling. 

The CPA you spoke to was right, there are tremendous tax benefits for what the IRS calls "real estate professionals" The basic criteria is twofold: 1) you must engage more that half of your 'working' time in real estate related activities. 2) You must spend at least 750 hours involved in RE.What is considered real estate involvement?