Drop your experiences below!

I certainly want to err on the side of caution in terms of investing in a pricier asset (at least in my RE experience thus far). 

I would be happy to share my experience in knowledge in this area (MA and RI) as I continue to look to build my portfolio. 

@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

I can absolutely understand how these experiences have drained the joy out of owning rental properties.

Most agents paying for leads are inexperienced, which is why they need to pay for leads.Look for an agent with a minimum of 15 years of active experience.

The fire insurance companies dropped policies holders when they knew the fire was coming, in some cases, they're not even paying the full amount, and there's the case where some people didn't even have insurance.For those people who just want to walk away from this entire experience, is it possible that  morally-driven wholesalers can help them in a situation where not only the California government failed them, but also the Insurance companies?

Happy to chat more about my experiences if you'd like. 

My experience is that when people can afford to keep their expensive property, (sans a house), they rebuild.

So I am not telling you what do, rather I am just sharing my experience.