How hard is it for a person with high credit score but no income, retired to get a loan?

Personally I would invest in something relatively close to you, that you understand and have knowledge of.

Hello everyone,I’m a 18 year old electrical apprentice and I’m looking to do a full dive into real estate investing.I am in the union and earning base wage, parking, vacation pay, pension and full benefits are covered.I am saving about 400/w in a high interest savings account right now which is 60% of my pay, I am going to get guaranteed $5/h raises every year for the next 5 years.

Assuming the insurance premiums don’t significantly impact my cash flow (which is one of my primary goals), how do you assess the risk of taking out a loan under my personal name versus opting for a commercial loan that requires a larger down payment and comes with a higher interest rate?

This would require tenancy in common which lenders typically won’t allowTransferring ownership from personal names to LLC is straight forward with a deed transfer and re-assigning the tenant leases.

Premium increases are rippling through the market; the state is also always going to be financially strapped/high tax due to union pension commitments from past generations and the high tax, high services nature of Chicago.I'd highly recommend getting on a plane and driving around before you buy anything there. 

I submitted an offer that must have been competitive because the seller responded via email with a counter on terms, then called my realtor and asked if I had seen it in person.

Quote from @Renee Ward: In a quote for an umbrella policy, when I see it in writing it is labeled a personal umbrella policy with our primary home cars etc. 

If not in-person meetups or clubs, do you know of great online meetups?

It's called the Asset Island method, long used by HNW persons to great effect.