You must buy ALL OF THEM or you are out of the family.
You must also buy the DA 560 or you are out of the family.
Seriously, I can remember making a very similar post to this one shortly after I joined.
The only way to find out what lenses you want though, is to TRY THEM OUT. Seriously.
Luckily there's a relatively cheap way to accomplish this. All it takes is patience and persistence.
1. Read the lens database, scour Amazon, B&H Photo/Adorama/KEH, Fleabay. Learn the rough values of lenses.
2. Scan the marketplace, local craigslist listings, camera gear swaps, etc. When you see a lens you want, and if it's a good price (see #1), BUY IT.
3. You don't like it after a while? SELL IT. You can probably get the same amount for it, or close to. You may have to eat shipping, depending on where you bought it from/where it's being sent to, but at most that should be about $40-$50 per lens (at most. It will be hopefully well under this).
4. Accessories are the other thing that will eat up lots of $$$. It's hard to offload the random crap we buy to accompany our cameras and lenses (bags, cheap filters, etc.).
Oh yea, and your self imposed limit of $500 max spent per lens will be SHATTERED in spectacular fashion sooner than later.
As for your list, here's what I would do (bolded are things I have)
Wide:
DA 15mm F4 Limited
A spectacular lens. I bought mine basically on a whim because it appeared locally (used ones usually get snapped up pretty quickly). I have a gut feeling that one day this lens will pay for itself somehow.
WR:
None
Weather resistance is overrated, unless you're going kayaking, or are spending a lot of time in desert conditions. If you insist, get the 18-135.
Fast zoom:
Tamron 17-50 f2.8
I lusted after the DA* 16-50, but again a good deal came up on the marketplace for a Tamron 17-50, and I bit. So glad I did. It's silly sharp, and if I had to keep just one lens going forward for some reason, this would be a strong contender.
Some people prefer a little longer reach as opposed to a little wider field of view, and I think the Tamron 28-75 f2.8 is equal to its brother.
Daily prime:
Pentax F 28 f2.8. I've owned the DA 35 2.4, and it's an absolutely excellent substitute.
I am itching to upgrade this to the FA 31 though. Soon . . .
Portrait:
DA 70mm F2.4 Limited/
Pentax F 50 1.7
70 might be a little long for indoors, so you might find a fast 50 to work better. They're all good really.
Do note that I'm going to offload my DA 70 soon because . . .
Macro:
Tamron 90mm F2.8 Macro
Again, bought on a whim for a good price. This is my new longer portrait lens. It's so crackling sharp, as all Macros are. The DA 100 to my knowledge is its equal in the IQ department, and it's their intangibles and price points that separate them.
Tele-zoom:
Pentax DA/Tamron 18-250
I dislike changing lenses, so I favor the versatility of the 18-250. I have owned a 55-300 though, and it was a fine lens, but honestly if I really wanted a telezoom, I would get one of the Bigma variants.
Manual lenses:
None because manual focus isn't for me. If I want manual focus I'll just use my lenses above in manual mode.
Get some flashes yo!
Have fun.