Showing is how you earn the big EXP and money on v2 so despite what you see on other games and on v1, the more entries, the better. The higher the fee, the better also.
Basics can enter up to 5 while Premiums can enter up to 10.
To enter these shows effectively, you can open horse's pages by tabs (for those only with good computers) or by using "next horse/previous horse" navigation by starting with the very top horse listed on your stable page. Going to World -> Shows is a fast way to be burned out if you have 20+ horses.
Horses must be fed to enter shows or the game will let you know saying "This horse is too hungry." Once you fed them, you can press "Enter Shows" button on their page and it will lead you to a view of the shows that they qualify for.
Depending on the time of day, you will see that certain disciplines have not filled up yet. If you see entries over 30 with a 1k entry free, enter them. You will always gain that money back regardless of placement thanks to the show's formula. It's been proven that as long as the entries hit 13, you will get the fee you paid back.
In the example to the right, you can see that the entry fees are high but the entrants are way passed 13. You can safely assume that your horse will get you back the money no matter what you paid for despite their BS count/showing ability. This is how you make money real quick.
The only time the entry fee will be over $5,000 are on Saturdays. Rest of the days of a week you will see 5k at most so make sure you enter those higher fee shows to get all the cash you need.
After you select the shows you wish to enter your horse, you can press enter right after which will automatically enter you when pressing the button gets old. This allows you to enter quickly and go back to the horse's page or close the tab to go to the next one in line.