Don't enter every horse every week. It is tempting, but it only makes you money if you have a huge show string, with a majority of money makers.
Check out this post here by Mr. Moo... I've increased my show income by about 50% just by using this guide to cull/replace and enter. I've got about a 200 horse show string now, and I've been manually entering my unmanaged horses (broods) for extra cash boosts based on when they've leveled up.
I actually ran an excel sheet of my profit and loss
Income:
Daily Pay 4500 x 7 = 31500
Show Earnings 7 day total: 484,781
Total Income before Loss: 526,281
Expenses:
Rider Pay: -38600
Entry Fees: -380100
Total Expenses: -418700
Actual Calculated Income after Expenses Per Week: 107581 (Assuming I did all my formulas right in Excel... and wish I'd done one before I read Mr. Moo's article.)
So, not great. I did incorporate some mares into my search parameters to show and brood them out. Not sure if that will be a long-term income source or not, but I made sure I bought mares that don't fit my breeding program so I will resist the urge to breed them myself.
I'm sure there are a lot of others out there who can give better advice - I've been a random drop-in player for years now, which is hard to make EBs that way.
Looking at your barn:
Get rid of all 2yr + horses that are not PPP+ rated. Keep that EEE mare! Your unrated yearlings that are out of anything less than PPP parents need to go on Jan 1st. Not worth spending the money to rate them. I'd even fire the riders on them and let them sit (I don't put riders on my culls). Stay away from the Create Horse page... it is a wallet trap when you're trying to get started. Also, narrow your focus: what breed, what color, and then use that to keep your buying in line - that helped me tremendously.
Buy a few good show horses from Mr. Moo's advice search link. Fill your barn with show horses, and that one EEE mare. Breed her to an EEE+ stud, breed your other PPP+ mares to cheap EEE studs. Save enough money to buy a pasture and grow your own hay. Another barn for show horses. Once you are making a decent income, then add a few top-notch mares of EEE+ rating and breed them to top-notch WWW studs.
I get a kick out of breeding, so I don't follow my own advice very well (I have a barn full of EEE studs... ), but really, if you want to self-fund here, that's how you do it. When I had a 500+ show string, 100% were homebred, but it took about 2 real years to get them to make a good income.
Also, if you're of an artistic nature, there is some money in that, and I did lots of it real years ago to boost my resources.
Hope that helps, for what it's worth. I'm by no means one of the 'hard hitters' here, and there are so few names left that I remember from when I played seriously.