The biggest obstacle was getting a bank that would accept a signed lease as part of our debt to income ratio so that we could qualify for the next house.  

And thank you for the inspiring compliments.I have heard about some of the difficulties finding people of character there, and based on your comments, it may be as big an obstacle as anything else.

I recently got my real estate licence and became a realtor because I thought that was going to be easier to do my first deal when I had access to the MLS but now I realized that my big obstacle is doubt and indecision and I have to overcome that.

Further, I've seen some data that indicate that townhomes with sufficient outdoor space could begin to meet demand from demographic segments that are generally considered to prefer single family detached products (families with children, etc). 

Yes, the price point can seem like a big obstacle, but it is one that's easier to overcome than you may initially think.

I often feel that the biggest obstacle for new investors to overcome is THEMSELVES...often we just need to get out of our own way!

Last Friday we closed on our first property, a 3 bedroom, 1 bath, two story brick home in St Louis, with a detached two car garage.

With no w/d, detached garage, carpet, and a tenant wall. 

The textbook answer is to determine the NPV of the investment and base your discount rate on the obstacles that might cause you to miss the mark.

cash is king, less obstacles to close and the biggest one usually being appraisals.