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I think classic Whalers should have classic engines on them, at least as reasonably close to the age of the boat as possible. I assure you this adds value to a boat, as that has been my experience, provided the engine(s) look as close to new as possible. I also realize that many here would not agree with this idea. To each his own.

As for the Merc 150 I mentioned above, I had no choice in getting it, since it came on a Whaler I had to have - the Ribside 21. The original owner had repowered the boat with it, bought new, and it only had 420 hours it over a 12 year period, by Mercury hour meter installed on the boat of the same period. To me, a good 2-stroke is hardly broken in with hours that low. It is hours that count, not year of build. He also told me the enigne was bought as a leftover, and not actually put into service until 4 years later than it's apparent build year.

The other things of importance when buying a used outboard are:

1. condition of paint and decals, which sounds foolish enough? But it's not. Is the entire engine clean, polished and waxed, no greasy mess and with no skeg damage and paint missing? How an engine looks in cosmetic appearance is important, since it indicates how well the entire engine might have been cared for and how it was used. The exterior surfaces of outboards should be cared for like a car finish.
In the case of my 150, it passed this test, as you can see from the photos.

2. Is there any rust or corrosion, anywhere on the engine? This also indicates how it was used and taken care of. If either of these conditions exist, it is a no buy. Mine also passed this test.

3. Cylinder compression must check out. So must power trim operation - no bleed down or reverse kick-up. In my case, I got caught on the trim issue, but even the cost of the repair made the engine a great deal, since it has been giving me excellent service for 11 years so far.

4. as mentioned, engine hours count. If everything above checks out, under 1500 hours should not be problem.

So in my opinion, if all of this criteria checks out, as it did with the one I bought used on the Ribside,
maybe I just got lucky. I think any used, or completely re-manufacutred 2-stroke outboard can be a great deal for a classic Whaler. In my case, Mercury first made this 150 in 1978, in IDENTICAL form and shape to the 1988 model I have. So since the Whaler it's now on is a 1975, I put 1978 Mercury decals on it (not yet shown in the photos), and the rig looks as close to period correct as possible, with both boat and engine looking brand new. The boat draws a lot of attention wherever I go with it, including numerous offers to buy it - ("If you ever want to sell it, call me").