Either have quality from afar or run a more problem property locally for increased cash flow yield.Constant traveling far away to a lower class asset on continual basis will suck away a lot of your time and cash and you have to build that in to see if the extra risk is worth it for the upside.Investors like to keep problem properties close to home and re-cycle capital.

Just be aware that every extra daisy in the daisy-chain means: less profit to go around.

Never know, they might not do much but might give you an extra 500$ toward that problem.

I am also from San Diego and would love to go back a few years and buy some extra properties.  

ie. extra cash out means no hole!

He will hopefully have extra equity built in to the deal but the difference between a $30k and $40k house market wise may not be anything.

I would believe most people are not able to put extra cash towards a remodel after buying a house. 

You can deploy that extra capital now while interest rates are low.

If I had to pay an extra 1-2k to have it taken care of by a PM (which I will hire anyway since I don't want to manage the property myself - I'll be a first time landlord) I would rather go that route.Any advice / tips / feedback would be greatly appreciated.

But, it comes down to your risk aversion: many people in your position (1-8 rentals) have their rentals attached to their Homeowners insurance and then have a personal umbrella for extra protection.