GTOs are kinda neat, but IMO the resale thing is kind of irrelevant, because any modding money you spend is NOT coming back in either car for the most part(probably more true for the GTO than the S14), and the GTO is heading down in value quickly while the S14 isn't going to lose much in depreciation.
So ultimately I'd say it goes to what kind of car you want. The GTO is going to weigh almost 1000 lbs more than an S14 - is that something that you can live with? Yes, it's more comfortable, but that weight is going to make it hard to ever handle well.
The stock S14 SR notchtop turbo can pull out high 12 sec runs in a full weight S14, but you seem to be more into straightline stuff than cornering, so I'd go with a 52 trim GT2871R from the getgo. Get some 740cc injectors, Z32 MAF, mild cams and a tune, a FMIC and you're good to go with maybe an exhaust/downpipe. That should net a mid 12 sec car and give plenty of power from 2k RPM on. I'd say at that point you're looking at maybe $7-8k max. You can always go used/Chinese on parts to save a little money here and there at your discretion. Then whatever cosmetic stuff you want.
Mods for a GTO aren't exactly cheap, and a 350-370 rwhp S14 is going to be hard to keep up with in a much heavier GTO without quite a bit of money so take that into account too.
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