Yup, definitely more challenging the more branches the banks have.Again, my experiences tell me if you can reach a local bank with one or 2 branches, most likely locally/family owned, you can make a good connection.These banks do exist, it's just harder to find them.  

He went on to say that the application process is challenging, that there is no guarantee that you will get a home that I apply for.

The challenge of working w/ investors, if the investor is new, is time.  

The type of assets you buy will be related to how much money you have.If you are looking to place 50k etc. then it is more challenging.

I am barely starting and j am facing this simple challenge Jesse .

I have a unique opportunity and Id like some input and feedback on how to go forward...I own a duplex that I paid 150k for.

Also, its never too early to start; build your credit up by being reliable and strategic in opening and purchasing things and challenge yourself to learn cocontinuously.

I have no experience at all on RE and I'm up for the challenge.

What are the biggest challenges / downsides to the industry?

I see some challenges in the local market (high first cost, high property taxes, older building stock, etc...) but also see a lot of positives (low vacancy rates, stable real estate prices).