I'm in Tampa and, in addition to financing homes, we've built our share of ground-up spec homes here in the Bay Area.

If you are with a cloud brokerage like eXp or Real, you can just move and stay under their umbrella with a new state broker after you complete whatever Illinois needs for reciprocity.If they don't have a TC team, you will need to complete and upload all of the paperwork, but they should have compliance videos for you to do.

With respect to Tenant's back grounds, pets, rental history, job status etc etc we are always looking to learn but feel that aspect is strung and thorough.

Having not yet verified his income, he would well qualify.

As of right now, a lot of land investors are moving to lower cost marketing like cold calling instead of mailers. 

This is better than not speaking with your aunt, letting the problem linger and likely worsen.From my experience, in New York, the ultimate decision will depend on many factors and Liberal judges (as told to me by others with way more experience in these matters) can rule in favor of someone with a sob story. i.e.

You will, likely, be required to sign and comply with their auxillary agreements, which you may not like/enjoy if push comes to shove. 

I am also open to other areas like Dublin, San Jose.Thanks

Does anyone here hold a full-time job and do real estate investing on the side, if so what is that like?

It sounds like you have done this before and have a good plan in place.