I have quite a lot of different things from very expensive vintage instruments (which fortunately I didn't pay a lot for!), to very cheap guitars. For me (like Twinfan and others), it's the feel and the acoustic properties I care about. My 53 Les Paul is really light and has had the neck shaved so it is not as baseball bat like. That and the conversion to 58 spec stops it being a collectors item, but to me it is a brilliant guitar with a ton of mojo and unique character. I was lucky enough to get it for $2k before the used market went haywire and it will be one of the last guitars I ever sell (just before my 1960 strat!). I also have several custom made instruments from WezV, Will Scott, Nieal McDunnough and Bravewood, with an anniversary Feline Lion and a double neck WezV on the way. I know that these guitars cost me more than I will get for them, but it's the same with the Warmoth builds I've made. I'm lucky enough not to worry about resale value (because I hate to part with guitars), but I do care how much I pay. My Feline 2012 Anniversary will be my most expensive guitar in terms of cost, however I have been talking with Jon for years and love the feel of the Lions, so when this limited run came up and I was able to have a small mod made (using a wrap around rather than stop & bridge), that decided me. I also loved the look of #7 and playing it last month before it went for spraying felt like it was one of my old guitars.
With amps I have pretty much the same view. I have old Fenders and Marshalls and also Ceriatones, MJW and McIntyre custom amps. I started to get into them with John McIntyre many years ago and have worked on his stand at NAMM many times in the 1990's. At the moment my go to amp is my Class 5, but that is because I lost most of my speaker cabs in hurricane Sandy, and I'm still trying to get the house fixed before I replace them. My original quest with custom amps was to get the sound I wanted at a lower volume for recording and because I lived in an apartment. My favourite full rig is a 2 amp set up with a Silver Jubilee 50w Combo & a Fender Deluxe Reverb, however that's not really a practical set up for many reasons and so I started to look at other options (begining with a Sholtz Power soak on a Princeton Reverb and going through a few rack mounted pre-amps).
I have Bare Knuckles in many of my guitars and have known Tim for many years and go down to his place at least once a year. This is my decision as I prefer the sound of his pickups to many others that I have tried and I like his tone choices. Because I don't go for mint vintage guitars, many times they'll have SD's or DiMarzios fitted, so pulling the pickups and putting in BK's is really a no brainer. Same with my custom made guitars, practically all of them are BK's. It helps the the makers also like BK pickups, so they have an opinion too, which I can take into consideration. I've made some c--kups with custom pickups too (AV Apaches don't sound great - that's why Tim doesn't make them, but I convinced him to make me a set a long time ago!). It's all part of the learning process and I think boutique gear falls into the same space. Some are great and some are not.
I've probably wasted a lot of money through the years, but I don't regret it, as I have had a lot of fun too and met many people who share my views and passions. To me there is a point at which I have to say woah that's too much, and unfortunately the PRS Private Stocks are probably in that category. However, if people have the money I don't begrudge them the opportunity to own them (and truth to be told I could sell some guitars and get one if I wanted). I still like vintage instruments, so most of my money does go there (and into the house just recently). I was debating between one of the PRS Signatures and a 1971 LP Custom and 72 55 Special a couple of years ago, and went for the 2 vintage ones. I may still go for an artist model or modern eagle in the future, if I find one that suits me, but everytime I look at the cost of the private stocks I start to look at vintage guitars again!
I'm still interested in the reviews, just because I like guitars and amps in general, and I hope that they will save me some money by steering me clear of things I won't like. Though to be fair, I really like to try something for myself before I buy it.