This becomes an issue of cocern in higher priced properties with larger seconds, but if your loan is less than the lot value, you're probably in a much better position.Another issue that could apply to you is the recent CA investor requirements and being a qualified investor.

If you live in one side and want to STR the other, that won't work because each unit is its own primary residence.That said, I have clients who have successfully rented out a guest house/ADU in LA on a short-term basis and since they occupy the main residence, they are not bound by the 120 day limit to fulfill the primary residence occupancy requirements.

Is any rehab required? 

Lastly, if there is imputed equity, some lenders will give you credit for this but usually requires a story, and not merely being purchased well.

Please consult with a mortgage expert about that requirement before making a decision as this is not advice, I am not an expert.

They are an online insurer specializing in insurance for investors and investment properties.

With technology and on line title records, major loan servicers are set up to detect deed transfers in major counties.  

Mostly look at online reviews and maybe search the BP forums for others experiences with the same company. 

Effective property management in the Chicago market requires working with a trustworthy property management firm.

This would be our first new build and require rezoning approvals.