Depending on the lender and program your biggest hurdles might be credit score and income and time in job. 

My biggest fear is that if I ever were to quit my job, I would no longer be able to invest in more real estate (not sure if I would qualify for loans as easily). 

Rent out to roommates so I employ the "rent by the room" essentially.Pros:insane cash flowif your room offer is much better value than other places to live, tenants will stay awhilea small community can be built when your tenants become friends with eachothernever ending supply of tenants (at least in my area)Cons:CAN BE management intensiveWILL BE management intensive until you gain experience and know how to manageIf you employ this strategy, the BIGGEST risk/liability mitigator is being VERY clear from the start about your expectations and that you will evict if new tenant doesn't follow your rules.With my setup - I furnish the rooms and have all utilities covered. 

One of the Biggest Challenges I see for All Real Estate Investing Education Companies out there are Students not being able to take action which resorts to blame and failure.

The agent will have access to the biggest platform to get the property sold though, the MLS, so forgoing even a cut rate agent will create more of a loss than the agent fees themselves. 

@Jake Baker - That point is probably my biggest consideration.

Then he admitted his biggest mistake was not holding properties, so I asked why.

As for short-term financing, they are fairly easy to work with but the biggest hurdle is their internal credit model.

Biggest hurdle right now is finding a reasonable cleaner.

@Jonah Gunalda sponsor selection is critical—if you are investing with first-class sponsors you’ll mitigate one of the biggest risks in the syndications space.Start with this book.