Getting Travel Insurance is a personal decision. You have to weigh the pros and cons for your individual situation and determine if travel insurance is something you can risk.
Should you consider purchasing travel insurance? You should if you will miss the money you invested in the trip when something goes wrong or if the expenses of a medical emergency are more than you can cover. I think a policy that doesn’t include medical coverage is not worth having.
I get insurance based on my travel destination and the amount of adventure activities I might do. I don’t get insurance when I go to places like Europe or Australia, but I definitely have gotten insurance for my African safari and Mt. Everest trips.
I don’t worry so much about lost luggage, especially since I carry my important papers and valuables on me. When I visit another country getting sick or having an accident, my tour operator going bankrupt, or a natural disaster are good enough reasons for me to pay the extra money to know I’m covered.
I have used both Insure My Trip and Travel Guard in the past and can recommend both. I have been fortunate to not have to cash in on my policies and the peace of mind while traveling was well worth it.