But if you want to make your property a smoke free environment best to start asap.

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.  

In that environment you would be a real speculator to build.

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.

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.

. :-)And here I thought Illinois had one of the lesser lending environments.

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