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I am familiar with your boat, and know the original owner, Quinn. I am surprised the hydraulic jackplates failed, but salt water is a tough environment for those devices.

As an owner of an Outrage 25 Sea Drive Blank (a full transom boat), bought new in 1989, I can appreciate your problem. See the Personal Webiste photos. Back in 1987, when 25" counter-rotating engines first became available, Whaler solved the problem by offering the Whaler Drive models, which use 25"
twins. At this same time, they should have also raised the cut transom hulls to 30", but did not. On most of the commercial 22 and 25' hulls, beginning in the early 90's, they actually offered this as a factory option, and most were built this way.

In your case, my set of options/recommendations would be three, regardless of whether you repower with a single or twins:

1. Reconsider use of jackplates, specifically those offered by Detwiler, now a divison of Teleflex.
They are constructed of black and silver anodized aluminum which is needed for salt water use. I would consider the manual versions, forgetting the hyudraulic complications, expense and possible trouble. They make one with as little setback as 4". I have these installed on two different Whalers, and they are good looking and excellent and will not fail on you. See photos of my Outrage 19 and Montauk. Cost is about $350 each, and this will be your least expensive, but successful, solution. Combined with what the jackplate can accomodate in lift, plus the 5 mounting holes on Mercs, you can get all the height you need.

2. You may not be aware that an Armstong transom bracket, like I use, can be installed directly on a cut transom hull, with no modification to the transom needed other than closing in a few transom drain tubes. In your case, the top surface of the platform is installed 5" higher than the existing notch, efectively raising it 5" and keeping most water out. A dual engine bracket is recommended, with 6" side platforms. I am guessing this will be about a $4000 installation, and will require some steering upgrades and longer engine cables (buy Teleflex Xtreme premium cables).

3. Have the transom raised 5" to 30". On all 22 and 25' Guardians that BW manufactured in later years, this work was done after the hull came out of the mold, so it is something a good shop can do if they know what they are doing. Whaler Commercial Products may be able to give you some specifications on how this should be done. All of the Whaler Drive full transom boats were also modified after the mold.

Even if you are going to use a single, you want it to be a 30" model, to get the powerhead high enough.

I would stay with twins, and you might also consider the brand new 3.0 liter Merc 150 4-stroke EFI 150's for about 10K each. Strong and quiet, and lightest on the market, only 30# more than the DFI 2-strokes. I know those early Opti's you have been running are anything but quiet!