Get an umbrella policy.4.

I have a primary residence in CA and 5 investment properties OOS and I have insurance (and an umbrella policy on properties under my name directly) on all property.

Yes, we have a builder's risk umbrella line during the course of construction.

Just plan to keep expenses on a spreadsheet.  6) We got an umbrella insurance policy vs LLC - lots of forum threads on here about the differences and which one is best depending on situation.  7) An emergency fund is paying yourself, I don't sleep well whenever mine gets low.  8) For me, it would depend on your financial level, time to retirement, and/or if you have income you need to offset or not. 9) you need to figure out if selling with the up-to- $250,000 capital gains tax free for primary residence is better financially for you than renting as you'd be converting to a rental and potentially losing that tax advantage (takes a lot of monthly rents to equal that benefit), and talk to your accountant about the depreciation as I think they still value it as depreciated when you sell even if you forget to depreciate at tax time.   

If I decided to scrap the whole idea and just get a big umbrella policy with the exception of gross negligence are there really very many situations where the umbrella policy wouldn't hold up?

I just learned the laws, acted above board, maxed my liability protection up to $500k and had umbrella insurance. 

We also had an extra umbrella policy.Now that a few years have gone by and we've obtained more assets, meaning we have more to loose, it's made since to start an LLC and start to move things under its protection.Even if you get a good management company, which sounds hard to do, you'll still have to manage them and make sure they're staying on top of things.

I have HO6 insurance and an Umbrella policy to my name.

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

And having an umbrella insurance policy to help with the liability.