I do not recommend someone who has never owned real estate to do a fix and flip as real estate is challenging and cost prohibitive, I recommend if never owning real estate to start with an asset that does not need major repairs. 

However I did note that houses are mostly really old, e.g. 100 years or older... any idea if this poses challenges in things like lead paint presence, outdated wiring, rusty plumbing, etc., or have many of the homes already been updated?   

As for Cash flow, I think it depends on the deal structure as you mentioned, but also strategy/approach (cash flow vs building asset, holding long term).

I have considered doing a TIC/coop in San Dego but have the belief, without any data except for how I would value the financing challenges and tic risks, as being much greater than 10% price difference from condo price.  

I want to make sure that both of us feel like the deal is fair and equitable for the risks and rewards involved.Any guidance on how to approach these key questions would be greatly appreciated!

JMHO  I use a similar approach to paint sheen.

Working with a CPA or financial planner can help optimize tax strategies and ensure the best approach for your goals.This post does not create a CPA-Client relationship.

You can use that scenario as a learning experience when you may or may not encounter future challenges. 

I was approached by a young man recently who was contemplating doing exactly this.

Challenges?