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The best thing to do is wait for something major to happen. If you're pushing 250k+ then something will go wrong sooner or later. Wait till you have a BHG, or at least need a clutch. This will also give you time to go start saving.
When you do go to get a motor, pick the cleanest one you can find. Not the cleanest externally, but the cleanest one internally. Take a look under the oil cap, and take the valve cover off if the place will let you. Getting the cleanest motor possible will minimize the amount of rebuilding/refreshing you need to do. Timing belt and clutch are two high priority replacement items. Seals would be next priority. There are a whole bunch of things you could replace, but should not be necessary if you get a decently clean motor.
I've had guys successfully swap silvertops for just over $1000, including the wiring. It's a nice upgrade, is cheaper than getting a 16v rebuilt, and only somewhat more than just getting a decent used 16v.
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