Do the following routine every morning to win Gray. To ensure you have money and to keep the farm going, you must plant as much as possible every season and take care of your animals. Equip your watering can, brush (if you have a horse) and hoe (most important tool). Do not to buy any animals or tools (except the brush if you have a horse) until you reach 10000g for the first year.

Year 1: Spring to fall

6 a.m. to 7 a.m.: Water plants, talk and brush your horse (if present)
7:10 a.m. to 10:30 am: Dig at the mine until you fill your rucksack. Run to your house and drop two ores. Keep one ore to give to Gray. If there is still time, go to the spring and near the woodcutter's house and pick the magic grass or anything "sellable".
10:30: Go to the Blacksmith's. It will probably be about 11 a.m. when you arrive. Give the ore to Gray and talk to him twice. You can do whatever desired for the rest of the day.