Interesting thread...
Some issues :
If plan installing a larger OB, will it be on a side mount or middle built transom ? If with a SS OB mount Garrelic type, adjust all bolts and nuts to have minimum side play and replace plastic/acrylic mount with same size hard wood one, if not , OB will vibrate excessively and mount will crack open and lose dear OB going into the deep blue if not secured with rope or drag it down the sea bed if secured with rope, both scenarios are bad musique LOL!!
Sailboats are not designed to be planing hulls, are darn heavy to plane, just achieves fast displacement speeds whether hull rides inclined sideways with hard wind or while powered with correct OB's sizes.
Which 2 strokes outboards are available where you live ? If Tohatsu are available used or new go for a 30 HP one, weights10 kilo more than any 10-18 HP OB, will need to maximize a prop though. If going that route can give some nice tech parameters for engine to work as a champ powering Pedro 17 back to land safely.
OB's are factory delivered with medium pitch props, once break in period has ended need to dial a prop in order for OB to rev middle to max wot rpm range as usually loaded, which very few boaters go for..
The issue nobody uses larger OB's than 10 HP ones is mostly by word of mouth, besides distorts the sport, you've bought a sailboat, not a power boat, right. Add added OB weight along losing portability if need to put and remove OB from mount/transom constantly, worse if being an avid elderly boater.
These examples are from three different 24-30 footer heavy sailboats powered with 15-18 larger OB's, fully used when there's 0 wind to power their respective sailboats, Speeds are around 5-6 knots when loaded and as much as 12 knots in flat water cond when lightly loaded, all 3 with maximized props to rev full wot rpm when lightly loaded.
Happy Boating