As a litigation lawyer, my response to the OP would not be appropriate for this forum.
IANAL, but…
“Newer windows” without a frame of reference is not an informative statement.
The real estate agent may have made an assumption based on the other windows present in the shed.
“Newer windows” may refer to the fact that when the house was constructed, these windows were not the “new construction standard,” but a newer model than used in similar new construction in the area at the time. It’s quite possible that the original buyer requested and footed the cost for the “newer” windows and the ones in the shed are the ones that were originally in the specs, paid for and would have been put in otherwise.
Unless there was an active attempt to conceal a defect or you paid a premium for the property based on the “newer windows” designation (provided it’s determined that you reasonably determined that the designation meant the windows were replaced sometime after construction), you’ll probably pay more trying to litigate the matter than it’s worth.
I think Campion has nailed it here. People often have schizophrenic views of what lawyers do. On the one hand, there is the view that lawyers play needless word games to prevent justice, as epitomised by this comment from the OP:
This type of comment criticises lawyers for not seeking justice, but instead just being some sort of an attack dog that tries to prevent justice on behalf of whoever will pay the retainer, regardless of the merits of the case.
But then you also get this type of comment, in this case from the same person:
I would interepret that as saying that the OP does, in fact, want an attack dog who will just take the case and sue, regardless of its merits.
The job of a lawyer is to give the best possible legal advice to the client, based on all the facts. If that best possible advice is the unpalatable opinion that the client does not have a case, so be it - that’s the advice the lawyer is duty bound to give. It would be a breach of professional obligations to the client to give the client inaccurate advice, and then to start a law-suit on it, leading the client on, and charging for it.
Many lawyers have a reduced consulting fee, for a client who comes in. The first hour is often free, or greatly reduced. If the client wants more detailed advice than is possible to give in that initial consultation, well, yes, the client does have to pay, regardless of what advice the lawyer ultimately will give. It hurts to pay for bad news, but you wouldn’t want a system that the lawyer only gets paid for the advice the client wants to hear.
And really, that’s not much different from other professions and trades. If I take my car in to the garage because it’s not working well, and they start working on it, and then call me with the bad news that they’ve pulled it all apart and the transmission is shot and will have to be replaced, I don’t get to say, “Well, I don’t have to have to pay you for the work to this point because I don’t like the result.” I have to pay for the cost of the initial work that they’ve done on it, even if I decide that the car is past its useful life and I’ll send it to the junkyard for scrap value rather than pay for a new transmission.
To my mind, this is very much like my transmission example. The lawyer is advising you that in his opinion, you haven’t got a case. Why? For the very sensible reason that he’s successfully defended against this type of case in the past. That’s a pretty compelling reason for the lawyer’s advice. Far from being a sign of the lawyer’s “cockiness”, I would say that’s the example of a lawyer who will give unpalatable advice to the client, as required by the code of professional ethics. At the same time, the lawyer says he’ll try it if the OP pays for it. That’s pretty much like the garage phoning me and saying, “Yeah, your tranny is shot, and if it were my car I’d replace it entirely, but if you want we can try to patch it together again - it’ll cost you about $500, and there’s no guarantee the patch will hold for any length of time.”
I may not like that advice from the garage, but they’re being upfront and honest to me, giving me their best professional opinion. And yes, I do have to pay for that opinion, even if I’m upset by it.
Perhaps this goes to the heart of your unhappinesss with the legal system. What is the “system” and how is it supposed to work?
The primary function of civil lawsuits is to compensate an individual who has suffered a loss or an injury of some sort. That’s the key requirement. If you’ve not suffered a quantifiable loss, then you won’t be successful if you go to court. The legal system is not there to patrol morality generally, or to prevent inaccurate statements, or to punish lies. If inaccurate statements or lies lead to loss, that’s may trigger legal liabilty, but without loss, no damages.
That’s the reason for this reaction from the lawyers that the OP has contacted:
This has everything to do with whether you have a case. If there’s nothing wrong with the windows, by your own admission, than what loss have you suffered? The civil legal system is concerned with repairing losses. No loss, no case.
The lawyer has already intimated strongly and for free that he probably can’t help you. Are you so mistrustful of lawyers that you don’t even believe that?
It’d make for a fun deposition though.
Q: Mr. Foo, please tell me in your own words what is wrong with the windows.
A: Well. Nothing is wrong with them. I just thought they’d be newer.
Q: Sir, you had an opportunity to have a professional inspect the windows before the closing, isn’t that right?
A: um . . . yeah . . . but . . . the inspector didn’t see the listing sheet.
Q: Why not?
A: I didn’t provide it.
Q: Why not?
A: ooooh . . .
Q: Sir, I need you to answer verbally. The court reporter has trouble transcribing gurgling sounds. . .
A: I’m not sure.
Q: Let me ask you this: According to your Complaint these “newer windows” were part and parcel of the transaction. Without those “newer windows” you would not have offered as much for the house, and might actually have decided not to buy it. Do you see where it says that? It’s in paragraph 194.
A: Hmmmm. Oh, Yes. I guess so.
Q: Ok. So you had the opportunity to have a professional inspector check those important windows out, right?
A: Er . . . um. . . (glances hopefully at lawyer)
Q: Sir, your lawyer can’t answer the question for you. Can I get a verbal response?
A: Yes.
Q: The inspector found nothing wrong with the windows, right?
A: Yes.
Q: Ok. Let’s move on to your claim for loss of consortium . . .
Well, fun for the defense lawyer anyway. 
I, and several other folks, have repeatedly asked the OP what he thinks his damages are - how much did he overpay because of the term “newer.”
He has yet to suggest a penny.
This is the kinda thing that makes this litigator very glad his practice is limited to federal appeals.
(Not responsive to the OP, but reminds me of one of my favorite legal mnemonics for tort liability. Dumb Blondes Can’t Dance. My wife, who teaches business law, came up with that one. Oh yeah - she thinks you’ve got a shitty case as well.)
CrazyFoo I am not a lwyer. This isd an amateur opinion.
I have a certain amount of sympathy for you, assuming that your description is accurate. The damage you have suffered is perhaps that you paid $1000 more than the property is actually worth.
I think - amateur opinion - that you ought to be compensated. But paying a lawyer to persue that £1000 will cost you $15, 000 or more. Best you forget it.
I see no further purpose in leaving this one open, at least not as a General Question.
Thanks to all the participants.
samclem