I can't afford to spend $5,000 on a pin either, but I'm sure I will eventually. You have to look at it like a savings account since these machines don't really lose value.
I started with one for $200. Then I bought one for $325. Then I sold some stuff on Ebay and saved some more and bought my Space Shuttle for closer to $1,000.
Then I realized I liked the newer games better, so.... I sold the 2 cheaper ones for a small profit, added a little cash to that and bought my second game for close to $1,000 (that one was High Speed, you will love it, ton of fun).
Now I'm in the process of saving up for a third game in that price range.

So once I have $3,000 in pins... it doesn't seem crazy that I would eventually sell them all at some point to buy one in the $3,000 range. Then you start saving up again and the process starts all over. I think even if you can't afford to just buy in to the "high end" machines immediately, we'll all get there eventually if we stay in the hobby long enough. I'm assuming this is the arc a lot of people have followed.

Take away from this is definitely get the High Speed, great game!

True, but you can figure your repair costs in to the money you are saving by owning the game instead of paying each time you want to play it

Absolutely, I wouldn't consider pins to be an investment strategy, just that they tend to lose less value than other collectibles (especially since you constantly use them). Unless you have the disposable income I can't ever see spending 10k on one of the really elite, highly sought after machines. Just saying that you can ease your way into a higher price point in this hobby than you would ever imagine being able to attain in the beginning.