I have contemplated doing a conversion like that with existing warehouse or office space but I am extremely new to commercial real estate investing and I think that is beyond what I'd like to tackle in the beginning.

In my particular case, I only had $50k in my SDIRA, and I found my options extremely limited.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.

Can you afford to live in Hawaii and self-manage, or do you have to hire a property manager when the good ones are extremely difficult to find?

Those are the two extremes, obviously most businesses are somewhere in between. 

I'll gladly accept any info on free leads as I'm still new to everything and I'm extremely eager to get started, thanks!

But 2-4 units is Chicago is extremely complex with 100+ year old buildings, Chicago zoning, department of buildings with violations and inspections, plus the RLTO. 

They point to extreme heat as proof, but discount extreme cold.

Oceanfront homes are extremely limited and commonly ask $1.6M+-$2M++ in the center of town it can be very difficult to secure an STR permit due to saturation (active neighboring vacation rentals) requirements.Lincoln City offers a variety of oceanfront home options, the challenge with oceanfront STR's in Lincoln County is that actively licensed STR's do not transfer and would generally be subject to a lengthy waitlist.

The biggest hurdle right now is interest rates, it is extremely difficult to buy in a popular market and actually make a profit out of the gate.