It's a declining biz model.....the city is trying to crack down on them, and insurance co.s are pushing back on the testing charges (which is where the profit is).

*I am not a CPA, tax professional or a lawyer*I cannot give legal advice, so all of my advice is illegal advice.As far as I know, section 469 of the tax code is what allows for the "STR loophole". 

You want the people who find the cracks because that is how you get better.

Its proximity to major attractions, businesses, and vibrant city life ensured strong demand from both tourists and professionals.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

The bigger challenger with this arrangement is finding contractors that have the financial wherewithal and general professionalism to submit true invoices for work completed and willing to let it sit out there for sometimes 2-4 weeks until the draw comes in to be paid.  

As mentioned, the bigger Sponsors are very professional and report very well. 

You always hire professional cleaners if it's an old person's home and construction cleaners if it's a disaster area.

How do I educate and reach the young(ish) professionals on the value proposition of these kind of "starter homes" to build equity, learn property management and save a ton of money relative to single unit purchases? 

the first step that I would take is to find an investor from the realtor in your area and you can build a lot of your network just piggybacking off of theirs with their recommendations of contractors and other professionals biggerPockets has a great tool for finding realtors.