We tend to like what costs the least and returns the most.I know this only vaguely answers your question but you asked a very loaded question.  

Hey @Raymund CharfaurosI'd need to know a little bit more about how much weight you place on each metric and your target returns; but I am almost certain you'll find that your two goals (increased cash-flow, continuing to have an interest in San Diego RE) don't necessarily have to be mutually exclusive.There are two factors playing in to your favor here:1.

Which would 'save' me $695/month in rent, but factoring opportunity costs of missing out on $250/month also carries some weighting.

Saves loads of time and that's just one example of the time savings. 

The tenant continually repeated while loading the truck, "my landlord saved my life, I cannot thank her enough!"

Here are some of my recommendations.Cut your debt load to as much as possible.

Make sure you are grounded in the knowledge that regardless of your prep there will always be surprises and there will always be tenants who you should not have rented to... and some of these can cost you a boat load of money...so just prepare for it.7.

The disadvantages I hear people say, in my opinion don’t hold that much weight.

@Luke Diem  Using borrowed funds for any portion of a down payment on a Conventional or Commercial loan are forbidden - - you certify that to get the load. 

We got a pickup load of trash from around the property cleaned up, did some general yard work and mowing around property to clean up place, and got to meet the neighbors.