I’m wanting to be prepared and educated since I’m new to this and looking for advice.

By 2030, we want to have grown a portfolio of over 100 units, created a property management company that manages an additional 100-200 units, and, finally (and most importantly), we will have established a non-profit that is focused on quality, affordable housing that specializes in providing housing and resources at/on the "services cliff" alongside financial counseling and first-time home buyer education in our target area.Our target area is the Springfield, MA and Hartford, CT areas with dreams to expand to Central Massachusetts (Worcester, MA), Southern New Hampshire (Nashua, NH), and Southern Connecticut (New Haven, CT).Would love to meet up with likeminded individuals in our area!

Education here is probably all that is needed.  

Avoiding Licensing Requirements and OversightBeing licensed often means adhering to strict state regulations, such as disclosures, fiduciary duties, and mandatory continuing education.

Unfortunately, this problem waste a lot of my time that could be spent on other investments.I have used the same tax professional for many years and he is very educated, but also much older than me and it's hard for me to understand all the reasons he has expressed why is better to put the rental on my personal tax returns.

I would thank him for his feedback and share that you made a business decision that is mutually beneficial (https://www.avail.co/education/articles/should-you-collect-r...scroll down towards the bottom of the page to see the comparison) which includes providing the tenant with a receipt and rent reminders.  

We have education in real estate principles, real estate law and real estate finance.  

Does that mean that education doesn't work too and is a bigger scam that what you are making this out to be?

Here's how I do my due diligence:1) Portfolio matching: (takes 30 seconds per deal)a) Have an educated opinion on where I think we are in the real estate cycles (financial and physical market cycles)b) Then and only then do I pick the strategies, capital stack, and specialized asset subclasses that make sense for that opinion.

Not saying it cannot be done but be aware that these programs I have heard good things about but also recognize timing and you may have a great education but bad time to implement