Sure, there are horror stories about investors who lost it all, but if you play your cards right and put a few safeguards in place, you will are very unlikely to encounter issues.In order to mitigate risk in real estate investing, you need to attend this webinar!"

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

Here are a few points to ponder:Market Volatility: How do market fluctuations affect our investments, and what are the best practices to safeguard against sudden changes?

Unless you can carry the mortgage on your own without renting just as a safe guard, I would be cautious.

For overlay zones I often look at this site:https://scoutred.com/Overlays are important especially since your lot is in Point Loma so there is a good chance you are in the Coastal Zone, and the canyons are often considered "environmentally sensitive" land, both types of overlays often require additional processes for permitting your project. 

I know property address is sensitive material so here are a couple of links to help with the zoning designation:Residential Based Zones:http://docs.sandiego.gov/municode/MuniCodeChapter1...Zoning Map:http://apps3.sandiego.gov/siteinfoweb/begin.doAs far as hard costs are concerned, I have heard anything in the range of $165 - $210 hard costs.  

This approach suits me because my main focus is on safeguarding against catastrophic loss, rather than filing claims for minor incidents. 

There may also be language in your HOA's governing documents about these sensitive notifications, and how promptly they're to go out to unit owners / homeowners. 

This is a complex situation that demands a sensitive approach, a thorough grasp of legalities, and a strategic mindset.

My current dilemma is that in May, all of my tenants/friends are going their separate ways - therefore I either turn it into a true rental property (managed remotely w/ help from a local person in case of time sensitive issues) or I sell.