Investing out of state was a Huge mental obstacle for me for many years. 

I have found alot of the VAs are doing it for the lifestyle, where although I have issues with English to some degree it's mostly cultural terminology that is the obstacle but I have people working extra hard to feed their family.  

When we do have kids, our plan is to look for a house that makes sense to build a detached accessory dwelling unit on the property.  

. :) The house by my brother has lot's of hidden issues.It is a 1926, 900-1000 sqft. 3br/1ba/detached garage with a breezeway.

It has taken a lot of growing to overcome the fear and obstacles that come with doing something as crazy as leaving a relatively steady career to being self-employed and doing something you've never done before.Even with the major headache and heartache I currently find myself in, I do not regret it as a whole.

My biggest obstacle right now is working with underwriters to get my rentals into long term loans and out of hard money loans.

But I think it's important to mentally prepare yourself for some of the obstacles you will most likely face.

What obstacles you faced?

As with rent control, every obstacle to eviction makes it harder for the next person to rent. 

Our biggest obstacle thus far is finding a lender who will finance shipping container construction.