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).  

The challenge in investing education starts with the fly into town gurus who don't know your market and just want your money with minimal support.  

Further, non-judicial proceedings in some states can be challenged.  

The increasing number of crowdfunding platforms makes it a bit of a challenge to decide which ones to look at seriously, and which to avoid.

That impression could be very expensive, time consuming and hard to defend against if a family member or government agency objects later on.  

They expect a lot from their students, but don't own their own shortcomings as mentors / teachers.Most folks come into REI looking for the same guarantees of income they would get from an employer: do what I tell you and I'll pay you $x every week.A lot of folks drop out once they start the process claiming, "I'm putting out all this money and not getting anything back".Even the group I'm connected with still has its challenges, but is the best I've found so far.Many of the gurus, mentors, etc. tell you to "treat the business as a business it will pay you like a business", but they treat their teaching / mentoring more like a hobby.

We are having challenges keeping the calendar straight across multiple rental site platforms.

Yeah, I certainly wasn't defending them, but was just outlining to people typical vs non-typical terms.  

Messing with the glazing or wood trim, especially on old windows, will be much more challenging if it's your first time.