Hmmmm....I usually always win Ride 'em Caballero after I decided to always use up my first money building inexpensive/$50 trees (third slot tree...the one that looks like a pompom..sorry..not a tree person
During that first few years the one construction office makes those trees actual barriers to the storms. While you get hit..well..i've never had a 20k loss, let's put it that way. Max, 5k. Mostly I just lose one farm on each storm. Try to use up all your money doing the tree barriers as the construction workers MUST concentrate on planting them and they won't if anything else is on their roster.
I usually do three longish 'commas' of cheap ($50) trees. One in front of the wharf. One near each bunch of the precious farms. This usually takes ALL of my 15k starting money. Of course the country houses and bunks are used, next in the game. I don't overdo with construction offices...maybe 2. My population never gets very large, so 2 corn farms support it very well. I ensure that these are the first protected. Rarely are they every blown down.
I initially convert 2 or 3 of the corn farms to sugar farms..but frequently check to see that the soil still supports this or that kind of farm well. I vary the money-producing crops...pineapple, sugar..but never the long growing coffee.
Good luck! Hope this helps:))