I don't know if you've played around with the feature request portal (it's under Help and Support in the top right, then Suggest a Feature).

Just curious on possible strategies or suggestions from anybody currently thats an agent in the Central Illinois or Chicago area.

Do you suggest file 1065 or be treated as disregarded entity on schedule E. 

Though my response might help others, common courtesy suggests you thank those who took the time to answer you.

If it is only one flip for now, I suggest you find a CPA just to advise you on State filing requirements, ensure you are claiming all write-offs and issuing 1099s, etc.

Any lender licensee or realtor licensee cannot suggest to treat people differently and they can never do it in real life.

Unless the medical condition meets the state criteria for early termination and that the medical notice does not appear to suggest that, you cannot terminate the lease outright/immediately but that you will begin to market the property for rental and upon securing an acceptable tenant, the lease can be terminated pending a satisfactory property walkthrough indicating no damages. 

Many would suggest against RE investing using retirement money but if you go into low risk opportunities it can be a powerful diversification method.

Airbnb price suggestions tend to run on the low side.

Quote from @Aaron Raffaelli: As the title suggests, I am just starting to enter the REI world.