If you need referrals for local professionals, let me know. 

He can tell you strengths and weaknesses of almost every player or team from any era!!

I am eager to learn and help out wherever needed.A little about me:I am a professional working in San Francisco.

Part of my plan was knowing what my strengths and weaknesses are.

There are small multi families that are well suited for young professionals or even older families. 

I suggest a professional for help when there is little data.

If occupied, establish a professional relationship with the owner (caution--if listed with another office or agent, be careful not to set on any toes). 

Build professionals around you- Lenders, Title and Escrow, Insurance Agents, General Contractors, RE Agents.

Are there any questions one could ask that could at least give one enough of a feel for the condition of the property to be able to make an educated guess, make the offer, and then adjust from there if necessary after I DO pay a professional to inspect the property?

If your intent was to hold the property for productive use and you can demonstrate that wit past practice, documentation of conversations with your professionals, rental agreements, actual rent, etc then you could indeed do a 1031 because your intent was to hold and something external changed that intent.And the unsolicited offer is the gold standard of something that can change your intent.