I think having the paint chips will bother me, the chips are small but there is a lot on the fender and front. Just wondering how resale is going to be affected by not having original paint. The chip is on the driver side door, I'll look into Dr. ColorChip.
At the risk of stating the obvious, black is the worst color in terms of showing paint flaws. In addition, once you do paint correction on black, it will make the rock chips and deeper scratches in the paint even more obvious. It is difficult to tell from the photos because of the glare from the flash; but, the chips in those photos are looking pretty extensive. My suggestion is that based on the condition of the paint in the photos, you do not want to put PPF on as is. If you want to do the PPF, I suggest that you either do a re spray first or try the Dr. Colorchip. If you try the Dr. Colorchip, you are going to have to do paint correction before applying the PPF. I suggest doing the Dr. Colorchip on a small test section of the car and then have paint correction carried out on that test section. That will give you some idea as to how durable the Dr. Colorchip is and whether the results with the Dr. Colorchip are going to satisfy you. Remember, once you have the PPF on any paint flaws become like a fly trapped in amber.
Your price for the PPF seems reasonable if you are doing the complete car. Your price for the paint correction seems out of the ball park unless your paint is really, really bad. If its that bad, I would think that you might be better to apply that money to a re spray. I would be inclined to get a second and perhaps third estimate for the paint correction.
With respect to your concern about the effect of a re spray on resale value. Original finish has value if the original finish is in good or very good condition considering the age of the car. Based upon your photos, I don't think your original finish is adding value and a re spray in the original color would likely add resale value. Re sprays in non original colors tend to be value destroying if you are trying to sell to a market that values original condition. I assume that you would be retaining the same color code as the factory finish.
As a final suggestion, go talk to the PPF guy about the condition of the paint. When I first enquired about PPF for the front of my car, the PPF guy looked at the bumper, hood and fenders and then did the "I can do the PPF if you really want it; but, you probably are not going to be happy with the appearance". His recommendation was repaint, wait a month or so and then PPF. If the PPF guy is a straight shooter, they may give you the best advice on whether you need to do a re spray or whether paint correction will do the trick.