I think Boxsters will eventually gain value simply from the fact that they're currently priced in the Dodge Neon range and therefore attract a crowd that's going to ruin many of them.

I think they'll attract people due to the price, but not the crowd you're referring to.
In the decade plus of driving this car I've been approached by all kinds of people asking questions, simply making comments all unanimously positive. One thing I noticed repeatedly is that many people who were currently driving "Dodge Neon range" cars when they approached were all very hesitant or absolutely terrified about the costs of running a Porsche, or any high end German car for that matter. The only people who did not run away when I told them what it costs to maintain, were guys who were in pretty nice cars already but didn't know much about Porsche. These tended to be guys in their late 30's to mid 50's, dressed well, maybe wearing a nice watch and just gave you the impression that they were established in their careers. And even since prices have fallen to below $10 for the first Boxsters, I've not seen ANY young people in these cars. All of the Google searching that comes up with IMS probably has a role in getting young people or people on limited budgets turned off to these cars. But I agree, a very high % of Boxsters will be in the scrap heap simply because defferred maintenance can quickly outrun the cost of buying the car in the first place. It's really a DIY'ers car, and one with space, time, tools and $$$ to install the overpriced parts... a small slice of the public.

I hope you're right about the owners, but there sure are some awful customs happening. Fender flares? Big wings?

This is an interesting point. To my sensibilities, I would expect younger people to be drawn to an affordable sports car like the 986 Boxster.

But I think that the threat of high repair prices drives off almost anyone on a budget - they take one look at $120 vs $39 for an oil change and walk away from the Boxster, never to return.

They all drive Subaru and save trees and animals with their purchase.

I'm younger (people tell me this, I don't feel that way) at 27, had my box for 2 years now. However Porsches have always been my dream car. The boxster was my dream car from a young age followed closely by the 2000 Carrera 4 when it came out.

So despite the high maintenance costs I'm just too infatuated with Porsches to own anything else, especially now that I've owned one. I love the look, the engineering behind them, everything. As such, I could never desecrate one like it was a Honda del sol. Don't get that and never will.

a guy local to me found a rusty 356 like that bought it for 3,000. He put it on eBay expecting to maybe get 5 -6 for it the bidding went up to 36,000

They'd all rather have more horsepower instead of a good handling car.

And the prestige argument doesn't work on a testosterone raged teenager that demands a truck or something manly.

That leaves little interest in the boxster for young people, those that would get a boxster tend to drive mx5s instead as they still are cheaper.

I like the look of this Ghia better and it's only $900.
56 karman ghia
Maybe I should pick it up, slap a few vintage Porsche badges on it and sell it on eBay.
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A 1973 911 RS 2.7 Touring went for just under a million this week in NY, so the high end values are still holding pretty well. Then again, it is bonus season on Wall Street...someone paid $1.6 million for Janis Joplin's repainted 356.

1973 Porsche 911 Carrera RS 2.7 Touring | New York - Driven By Disruption 2015 | RM Sotheby's

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These seem kind of too good to be true
 

1959 Porsche 356 1600 - $58500

Was the 1600 Craigslist Ad pinched from here?

1957 Porsche 356 Speedster - $45000

Maybe the Speedster is a replica kit? The ad doesn't say so, but it also doesn't say it isn't and this sounds like a kit to me-

"Beautiful, one-owner high quality 1957 Porsche The chrome and trim are all immaculate as well. The canvas top, tonneau and boot cover fit perfectly with all of the snaps and fasteners accurately placed on both car and canvas making"