But investing OOS intimidates me by not understanding the local area as much and relying on obtaining quality agents, contractors, and potentially property management.Does anyone have any sound advice for the best step in securing a long-term financial future for someone in my position given my location/circumstances (San Diego,CA)?

They always fall back on BS like "quality of finishes are different" or "the other house had nicer landscaping".

If not, you will at least be required to have a job offer with a letter stating your employment has no outstanding conditions.

However, I’m still not seeing quality leads.I get some inquiries but when I send a link to our prescreening form the potential tenants don’t “pass” the prescreening.

(Quality) Contractor relationships have been the hardest piece of the puzzle for me in Austin. 

@Eric Stugart Factors like overall property cost, down payment, quality tenant should be characteristics to look into as well.

I have found, at least in my market, that I get a better quality of applicant and if tenants know there is no "man" to screw over they will be happy to pay rent even in times of black swan events. 

They are not quality control.   

About how much to replace it with good quality shingles?

. - My concern with building new, is not being able to spend all day onsite to manage. only being able to go on site at the end of the day after work to see what was completed and to what quality.