Pyrrho = Philosophy.
I never took any of those Philosophy classes in college because I didn't think I was smart enough.
All I can do is memorize, not philosophize.
Crap, I can't even read.
One thing to consider is the wife-factor.
Is it a gamble to think that his wife will allow for future upgrades any time soon?
Will his wife allow for a $50 per month allowance towards the HT fund? Does he have to cut some other amenity costs?
It's easier to plan for upgrades if you have some kind of "fixed" HT funds.
But everyone has different priorities, and priorities change. My 39 yr old brother (bachelor, never married, no kids, etc.) would rather spend money on sports cars.
So he bought a Mustang Shelby? (I'm not into cars)
And he said he would just buy a pair of Infinity P363s after he heard my P362s. He does not care for subwoofers or projectors. All he wants is an AVR, 2 tower speakers, and a flat panel TV.
I did tell my brother to NEVER EVER buy Bose speaker systems, and he listens.
Also, he used to own Polk towers (the $200/pr variety

), and he hated them. He loved the P362s.
Spouses can affect things, both in terms of what one does now and in the future. In my case, I had a decent 2 channel system when I got married (the one I lived with for over a decade before I got my surround system, and then moved that decent 2 channel system into our bedroom). My wife loved music, but was listening to a cheap boom box before she heard my system. She appreciated the improvement in sound very much. We did not have a lot of money at first, and so upgrades were not done, though when our CD player died, we replaced it, even though it was not terribly easy for us to do. When we got our first surround sound system, my wife was not convinced that it was a good idea, but because I knew a lot more about audio than she did, and because I did not waste money on useless crap for my audio system, she went along with the idea. I was then smart enough to let her pick the movie rental for the first experience at home, with her keeping in mind that we wanted a film with impressive sound. (I had, of course, taken the trouble to properly set it up first.) Hearing that first movie on our new surround system, she then was convinced that it was a good idea. The upgrades since then have all been with noticeable improvements, and we are at a point where I am satisfied, even though obviously there is better gear out there. We also have some 2 channel systems set up, with the living room system having
Apogee Stage speakers. Those I got used really cheap (I almost feel guilty about how little I paid for them), with the idea that I would probably resell them, but they sound better than my Aurum Cantus Leisure 2SE (original U.S. version) speakers that we previously had in the living room, and so we are keeping them, despite the fact that they are much more obtrusive and much less attractive than the Aurum Cantus speakers (and much more difficult to drive).
(However, I don't think the Apogee speakers sound better in the high treble; those Aurum Cantus G2 ribbon tweeters are superb and produce treble as good as I have ever heard. It is the midrange and bass where the Apogee speakers are better, and they also create a sense of space due to being dipoles.)
Right now, I am not looking to upgrade anything, though I do from time to time buy and sell used gear as a sort of hobby, and so it is possible that I will obtain something to upgrade something somewhere, though it is really doubtful at this point, as I like to keep the price down for my hobby of playing with used gear, as this way if I get stuck with something I can't resell, it will not be a significant loss.
For someone on a tight budget, they often need to decide between having a decent pair of bookshelf speakers, or having speakers that are more full range but are crappy (it costs plenty extra to have a truly full range and good speaker). When I was a teenager, I wanted to have lots of bass, and bought and sold several pairs of speakers, trying to get something that had significant bass and sounded decent. At my budget, there was no such thing, and so by my early 20's, I decided it was better to have most of the frequency range reproduced decently than to have it all as crap, so I settled on a good pair of bookshelf speakers, which were my main speakers for many years. Although I really like having deep bass (very few people buy a pair of SVS Ultra subwoofers without really liking deep bass), I would much rather have a good pair of bookshelf speakers and no subwoofer than to have a full range speaker that was crap. Now, of course, with subwoofers being common, one can add one later if one wishes, which makes for a very reasonable upgrade path for one's good bookshelf speakers.
And with surround sound, there is now the decision between one pair of good speakers versus a bunch of crappy speakers, and I have already stated what I think regarding that.
As for Bose, my wife thought the little cubes were cute, and liked how they were unobtrusive, but I explained about their sound, and she was then not interested in them. Since then, we have been to a party at someone's house in which there were the Bose cubes playing, and afterwards my wife commented (to me privately, not to our host) on how crappy they sounded. Though she believed me previously, it is nice when she knows absolutely that I was right about something.
Now, if I were the sort of person who spent thousands on power cords and magic pyramids and other foolishness, my wife would be very interested in curbing my spending on audio gear. But I never spend money we don't have (a wise decision, no matter what hobby we are talking about), and I only spend significant money on things that matter. I also am not impossible to please, and so I have pretty much reached the limit, and really don't plan on upgrading any of my audio systems (the TVs, on the other hand, I would like improved, but I am a patient man and will wait for prices to drop further, and will "suffer" with a 42" 768p main TV in the meantime).
As for philosophy, I think it is a good thing to study in order to live a good life. If you want some good practical advice, I recommend reading some Epicurus:
http://www.epicurus.net/
I am not endorsing his position absolutely, but he does give very practical advice on how to live a happy life, particularly in his
Principal Doctrines and
Letter to Menoeceus. Epicurus was remarkably modern for his time, as he had a primitive atomic view of the world, but that is not terribly important for his advice on how to live a happy life.
A lot of problems that people have are brought on by themselves, and one can avoid most of those problems by following Epicurus' advice. Obviously, those are not the only problems one can have, but for quite a few people, those are their biggest problems.