I’m halfway there and this is what I do.
Connect to harvest moon another wonderful life to live,this is also to get the sea cottage.
Then van will come to the Inn on Wednesdays, he is not of use yet.
Make friends with Won and sell him things like golden lumber {which you get on winter for helping the mayor.} Van’s favorite which you receive randomly and collect about 100,000,000 gold to buy the TV changer from van and sell that to Won for enough, or play his apple game and win 10 times then take all 10 flowers and give them to the harvest goddess where you will receive a flower you can sell Won for more then enough.

in summer, fill your whole field with pineapples
in fall, fill you whole field with sweet potatoes
in spring plant cabbage or pumpkin
during the horse races, bet the same on every horse and trade in all your medals for broachs(you must bring your basket with you)
then ship the next day
also sell green peppers!