Regarding "originality":
I understand (by reasoning) the desire to own something "original"-- the car Stirling Moss drove, the hat Lincoln wore, the bed Washington slept in, etc. But on an emotional level, "originality" does almost nothing for me for a couple of reasons.
I'm a hick-town tradesman, descended from a long line of builders-- men and women who pieced together quality materials, and created something greater than the sum of their parts. There was a time when almost everybody understood the concept of value added-- real estate was improved with the construction of a building and cars were made better by modification. There is a vast difference (in my mind) between a cobbled up repair using the materials at hand, a "correct" repair using OEM parts, and a modification which corrects some flaw and makes a machine run better than it did "as new". This is the very definition of a hot-rodder, as opposed to a mechanic.
While an old school car is cool, seeing what old-school men with a similar mindset did to improve it is of much greater interest. This is why I'll always be an air-cooled guy. The engine is improvable. Legend of the Sainted German Engineer aside, there are so very many flaws in the Type 1 design that improvement runs the gamut from low-hanging-fruit right through very involved re-engineering of entire systems. Taking an 80 hp engine as far as it can go is a pretty interesting proposition to me.
This kind of hot-rodding can't be done in any substantive way to a modern car, which is why I'm grateful for them as a hyper-reliable and comfortable transportation appliance, and completely unattached to them emotionally. My daily driver doesn't need me in any way. An original 356 or 550 (while important and beautiful) are vehicles begging to be improved and even to be reimagined.
I'm cocky enough to think I can do it better in 2020 than a struggling German shop could do in the 1950s. If I understand the essence of an early Porsche, I derive a great deal of pleasure in doing the same thing Ferry and the boyz did in my own way-- keeping the template, but rounding the car out as I see fit.
The other thing that turns me towards a replica is the investment value of originality. I (personally) think less of someone born rich or strong or beautiful than I do of somebody who worked hard to remake themselves into something that far exceeds the raw material they were given. It's not that rich, strong, or beautiful people (by birth) aren't rich, strong or beautiful (or that I can't appreciate that)-- it's just that they didn't do anything to get that way. I say this as a guy who had a lot of advantages in raw material at birth and frittered most of them away-- I haven't even lived up to my personal potential, let alone exceeded anybody's expectations. I really respect those who have.
So, to that end, I honestly like a Singer 911 a lot more than a perfect, low mile, numbers matching 911R. I like an Emory Outlaw more than a 100 point 356 restoration. But I don't like either of them any more than a really nicely done and well executed fiberglass replica. I couldn't care less about whether or not the VIN came from Germany or not.
The thing that turns me off "original" stuff most of all is the fact that for most buyers, this is a vanity purchase-- a measure of wealth and taste, as opposed to a measure of capability and intelligence. The automobile as a totem for wealth is a bit like the smarmy guy who marries the supermodel-- not because he's excited by the prospect, or even because he particularly enjoys her company, but strictly because it makes him look and seem more wealthy or powerful in "having" her. These are the same guys who can't and don't drive their 6 and 7 figure classics, and don't really know much about them at all... except that they are worth $1.2M or whatever. I don't want to be that guy. I don't even want to be a knock-off version of that guy. It makes me embarrassed when people think I want to be a knock-off version of that guy. This "look at me" thing is one of the reasons I hate entering car shows. If I do enter, I park the car and walk off to look at other stuff.
One of the things I always enjoyed about owning my plastic fantastic is that out here in F150 country, nobody but a car-guy even knew what a 356 was. With the rise of Speed Chanel, etc. on cable, everybody is becoming familiar with them (as totems for wealth), and now I wish that the original market might collapse. Then my car could be judged for what it is, as opposed to seeming like a dime-store copy of something super-valuable, like a photocopy of the Mona Lisa run on a bubble-jet printer using generic ink.
So-- the owner of 550-082 can think of himself as a protector of the priceless, but his car does less for me than Bob Carely's speedster with the 964 engine and transaxle, or Marty's turbo Subaru car, or Danny's no-nonsense 550, or Anand and Ed's lost-in-the-details recreations. I can say (in all humility) that none of them are as cool as my car is to me-- not because my car is functionally better (it's not) , but because what I have is an extension of my vision of what I wanted my car to be. It's mine.
That's worth more than a hundred German VINs to me.