Diamonds in the Rough vs. Store Bought Diamonds

I've been casually horse shopping for, well, my whole life. 

My first two horses were what I'd consider Diamonds in the Rough. As I'm gearing up to be a horse owner again, I've been wondering if I should stick with that routine, or do I just go to the diamond store?

Junior was 7, broke but unmannerly and unrefined, and cost me 4k.  He was being used as a trail horse.  Five years later we were showing the full slate of all-around pleasure classes and placing well in most of them. I had some training rides put on him in the beginning but I never sent him to a trainer.  Before I lost him he was appraised at 8-10k. 

I don't have the original photo he was advertised with, but it was pretty "backyard".  I mean he didn't look like a professionally marketed horse. 

Huck was 7, very well trained, but nearly feral from two solid years of solitude and minimal human interaction and cost me 4k.  He was sold as a "trail horse with reining training".  We attended many clinics and had many lessons and several different trainers hopped on him during the two years I had him, but I never had him in training - I'm still not sure if that was a mistake or not. 

This is the photo he was advertised with when I bought him:

And here are the gorgeous photos he was advertised with when he was sold again 5 weeks after I sold him. 

I don't know how much he went for, but I think we can all agree that he looks like a fancy expensive show horse in the last two photos, and a dumpy yard ornament in the first. His blaze and how wide his feet were set were what made me look past the horrible camera angle and sour expression.

This last year I also brought Kevin back from an overweight/unbalanced pasture ornament to a soft balanced handy horse and we won the Open Division at our Ranch shows.  He's never been to a "ranch" trainer, but he was professionally trained for pleasure by a reining trainer.

Even from the start of my riding career I was riding borrowed horses that were never as fancy as the other kids'.  I LOVED the horses I got to ride and they were good to me, and so was the wonderful woman who let me ride with her.  I was so proud as a 4Her to win champion or res. in ALL FOUR divisions at my last 4H show, on a $500 borrowed horse, in borrowed tack. Champions in Showmanship and English.  Reserve in Western and Contesting/Games - all with the same horse. 

So you can see, in my history I've always had to make the horse.  I've never been handed a professionally trained horse in show-ready condition and gone into the discipline they're trained for.  This is what I call a Store-Bought Diamond, and isn't it what everyone wants?  Is it what I want this time?

My current plan is to become a horse owner again "in the fall".   It's a soft goal meaning somewhere between now and next winter.  The longer I wait the more money I have available for the purchase price, since I've been squirreling away money since I'm not paying board. And I'm sure I'll need some new equipment, at least a new saddle pad... it's time for a 5 Star......

Will I buy another diamond in the rough?  A horse with good blood, good bones, that fell through the cracks, or just with untapped potential?  Or will I splurge for the store-bought diamond and for once in my life not be the kid on the backyard horse?   Or do I splurge on a fancy youngster and put it in training until it's ready for my getting-older-every-year ammy butt?

Here's my unicorn list:
MUST-HAVES
AQHA or APHA solid/minimally marked
Gelding (I'm too moody for mares)
4-8
14.2-15.2
walk, jog, lope, back, lead change
Smooth gaits
Pleasure horse brain
Ranch horse athleticism
WANTS
Pretty - open to all colors, but needs to catch my eye. Life's too short to ride ugly horses.
Good Hair
No pink nostrils - they always look dirty
Not too much white - see above
Excellent conformation - sue me, but conformation class is an easy way to get points
Barefoot - baby sliders during show season are fine, but I don't want to have to shoe.

So do I buy another <5k 10-15k="" and="" buy="" diamond="" do="" go="" i="" mark="" nbsp="" or="" p="" polished="" project="" the="" to="" up="">They all cost the same to feed. 
What's your show-horse buying strategy????