In case you haven’t read the previous responses or haven’t walked a mile in a landlord’s shoes. 90%+ of your problems are caused by your local/state government that you seem to be giving a free pass.

Petersburg for over 30 years, I can attest that the last two big hurricanes caused significant damage, but they were the first in a long time.Condos and townhomes tend to perform well, especially if they're located on the Intracoastal Waterway or within 3-5 miles of the beaches.

That might cause you unnecessary stress and lead to dropped balls for your clients. 

Did they previous take on bridge debt and has that caused them undo "pain" in the recent years?

This concerns me about the potential to maintain a solid tenant base and would likely cause a higher vacancy factor.

@Dominic Holt what's causing the property to run at a loss?

Quote from @V.G Jason: The first and foremost reason most people don't work with BP agents is cause 99%  of them are absolute trash.

I would love to make a move before the end of the year and so I keep trying to decide which of the following is best for me:1) Buy 1 more expensive CA property near here, and thus a better tenant (less likely to cause issues), but lose a little bit of money every month due to the current numbers, while hoping for future appreciation? 

They got evicted and caused $4,000 in damages over a 5 week span.The 3rd property had a tenant stay for 15 months.

Having all Section 8 tenants may cause you to have a higher cap rate on your exit due to a higher headache factor surrounding Section 8.