How can I find out if someone has a history of suing others to get money damages?

There are easy ways and hard ways to get this information. The hard way is to go to various courthouses and conduct a search (under his name) or possibly track this online (through a court records search - civil cases). Or, you can locate companies online or in the phone book that handle these types of investigations, and can tell you what they find (this can be costly, if the areas searched are vast). The easy way, and smart way, is to wait to see if you are sued. If so, the civil discovery process allows you to send written questions (interrogatories), or to make written demands (requests for production of documents or requests to admit) wherein he will have to answer, under oath, all of your relevant questions. If he lies about this information (including willful omissions), and your investigator later shows that he misled the court, all sorts of sanctions (including a possible dismissal of the complaint) can be imposed by the judge. Plus, the judge can award you the costs of having to prove that he lied. Your homeowner's insurance MAY cover some litigation costs, but typically will not for intentional ACTS (called "torts" in our legal system). Keep up with ell expenses, lost wages and other monetary damages, in case your State's laws have "loser pays" statutes.

It depends on how much money you want to spend. There are several investigation companies in California that could provide you with that information, and you may wish to call a few and see what it would cost. You could also try to do it yourself -- if you are limiting it to cases he may have filed in San Diego Superior Court, then you could go to http://www.sdcourt.ca.gov/portal/page?_pageid=55,1056871&_dad=portal&_schema=PORTAL and run the "party name search" option.