Ideally, I’m looking for someone with solid knowledge and would be willing to walk me through the process step by step.

I attached some visuals to give an ideal of the type of area. 

I’m ideally looking to buy that first property in San Diego.Thanks

Investing locally would be ideal for sure.  

It isn't having paid off properties that offers security, there are still taxes, insurance, maintenance and management involved. 

I think doing a 1031 would be ideal.

Quote from @Shakthi Kamal: If you don't know the answer, choose the umbrella insurance.

Fix it.We eliminate as much landscaping as possible: we take out flower beds and most decorative features, ideally, lawn mowing is the only job tenants have to do, because we know that's all we can expect from most.

Any help is much appreciated - obviously a short term rental would be ideal, but it looks like thats out the question for now. 

I suggest focusing on building your "Core 4" team—agent, lender (one who can finance both the purchase/rehab and refinance is ideal), contractor, and property manager.