As a general rule, you can't can't offset active gains (from flipping, other short term gains, or from  employment) with passive losses (from real estate, stocks, or whatever).  

Besides rental price and advising the owner to do more work / clean up on the property, what levers for marketing does a good PM company employ @Matt Speer?

You want good schools, population stability, strong employment/average income, etc.Finally, narrow it down to the type of property you are looking to invest in: single-family, multi-family, short-term rentals, etc.I recommend "Long-Distance Real Estate Investing" by David Greene for more details on how to evaluate a market.

Mostly with taxes and stuff like that - qualifying for a loan is definitely the biggest obstacle because of the whole self-employed thing. 

This article examines some of the key strategies that can be employed to expand your real estate business.1.

-thorough analysis of local economy, employment trends (and employment forecasts), availability of tenants and demand for rental properties versus supply of those types of properties.

You have to evaluate: Your current employment income vs bills  and longevity / foreseen relevance.   

I could have clarified better, I intended to use a 401K loan not pull out directly and I’m aware of the risk associated of it counting towards taxable income if I lose employment.

He has a master's degree from the University of Chicago, and has always been employed but has been renting his entire adult life.

Hi,I understand that the Employer (Single member Sub-S) contribution is tax deductible for the Company, however the Company pays both side of the ss/medicare (15.30%) tax.