A good friend of mine has a real estate related service business he wanted to scale.  

Hey @Scott Trench unfortunately real estate losses (active or passive) will not offset portfolio income from stock sale gains. 

Unless you have a Roth, you can easily pay much more in taxes by investing in real estate through an SDIRA.

The Real Estate Rookie podcast is such a great resource—you're off to a fantastic start.

But what you’re likely wanting is a real estate cpa that can handle your tax return and advice. 

The best part is the free CD is nothing more than a bunch of vague suggestions about how you can make all this money in real estate and vague bragging sessions about how he has been around so long and wants to give you all his knowledge before he croaks (paraphrased) Someday I will be completely immune to the crooks attempts at separating me from my hard earned money.

Here’s my honest advise; consider studying for and obtaining your real estate sales license, and obtain a part time position with a real estate agency that will provide training, guidance, and oversight.  

It's a super affordable real estate market where you can still find deals that hit the 1% rule anywhere from $120-180k for a single family (or $200-250k for a multifamily) purchase price.

I am a recent college graduate who worked in finance immediately after college, but knew that real estate was the path I wanted to eventually go down.

There comes a point where having a real estate-savvy tax preparer outweighs your time learning a new software.