I hear you about Appfolio--I have not signed up for the demo, I was turned off by their website that provides zero info (there is literally only one accessible page!) 

Pool house with plumbing Additional ~ 300 sq. ft. shop/storage buildingProperty on corner lot with 2 extra lots backing up to the end of a cul-de-sacPossibility of converting one of extra buildings to office for side-hustle/LLCGarage Appt #1:Connected to main house by a shared roof and connected breezeway~ 900 sq. ft. with kitchen/full bath/laundry and separate access/entry (stairs)Efficiency Appt:~ 800 sq. ft.

The cons are that you will have force saved money in a manner that you cannot easily access to increase your net worth and income.

You can find one online with a quick Google search or feel free to DM me and I can send you the one I used.

I have access to about 150k to invest and looking for some advice.

Also, I am focusing on the DuPage market so far because of my accessibility. 

I’m looking for an accessible Meetup that is set up as an open meet and greet.

Just my messed up mind running through thousands of things on my plate.When I am just in a relax mood, I like the blues/ classic rock To Learn it's usually a class (online or in person) where I take frantic notes (that I never look at) to associate hand, mind, ears.

Your best bet is to contact a Farmers agent as they will have access to all 3 of those companies.

I will echo what @Thomas S. has said.No matter what you read, you need either money or access to it in most cases to make it in this business.Learning how to do the work, even on a basic level, will give you a lot of knowledge and save you money moving forward also.