The biggest factor to consider is the new interest rate since it’ll likely be higher than your current 3.2%.

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). 

The hurdle that we are facing is insurance.

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 big challenge is the inspection process, which can feel like a hurdle.

However, I have similar hurdles as many do in getting their first property.

Tons of hurdles.  

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. 

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.

My only hurdle is the fact that I don't know the Real Estate Investing industry that well, so I don't know where or how to find the right documents for my wholesaling transactions.I've began generating pre-foreclosure leads, which I am able to filter out just ones with high equity, owner occupied, and no auction date, yet.