I'll start with the Axios interview I gave back in December and was published in January  Case and point, the low skilled Agents will be pushed out as there is now less low hanging fruit out there for them.The Elite Agents who have been superior to the low skilled Agents in everyway except for the willingness to work for a low wage, will no longer have to compete with 1,000's of low skilled Agents offering their services for a much lower price than the Elite Agents.Fewer low wage Agents means all that money rolls right back up to Daddy.

I am no way an expert but it does seem to me an easy way to do this is to get a RE license hang it with a broker and when you do your tax return they ask for occupation and you say real estate . 

I could sell the condo and "exchange" for something hopefully bigger but I'd love to hold and hang on to the San Diego property.

I have cold called and talked to over 1,000 people, the ones that get mad just hang up.

And then those that want to make a career but just dont have the skills or the financial security for the start up ( apprenticeship ) to hang in there to build a base of business.

I had a friend attempt a house hack in Conshy that almost ended in disaster and love to hang at Guppy's!

I've seen way too many people who "can't" work with these issues go out to parties, hang out with friends, go shopping, playing xbox all day eating sugar, etc.

Welcome to Chicago.  1st there are a ton of meetups where you can hang out with investors and discover contractors, agents, and lenders. 

Should I hire an inspector to walk properties with me and then get a contractor to look at the report for my first few deals until I get the hang of it? 

No pressured selling or pitching, just investors hanging out and talking shop.