I do not have any actual data that I myself have compiled about an OUTRAGE 25 with 250-HP or 300-HP, but I can make a prediction on the speed increase that will occur if your boat is re-powered with a 300-HP engine from its speeds with its current 250-HP engine.
My prediction is based on the work of naval architect George Crouch who developed a formula for predicting the planing speed for moderate V-hull boats based on their weight and horsepower, along with a coefficient that encapsulates the hull form and speed units.
Using your data for 250-HP, to predict for 300-HP will be quite simple. The only assumption will be that the total boat weight will remain the same. The top speed will increase by the ratio of the horsepower change to the 0.5-exponent.
As your boat is now able to reach 44-MPH with the 250-HP engine, with a 300-HP engine the top speed would be expected to increase to (300/250)^0.5 * 44 = 48-MPH.
I have developed a calculator based on these principles. See
In your instance, it is really not necessary to know the weight or the hull coefficient, as the only element assumed to change is the horsepower. If the new 300-HP weighs more than the current HONDA BF250 (which would be hard to imagine it could), then the increased performance would be reduced due to the extra weight.
For the classic OUTRAGE hulls of the 1980's the hull coefficient is generally thought to be in the range of 180 to perhaps 190.
My calculator can also deduce the total boat weight, so assuming the hull coefficient were 180, your total boat weight is about 4,180-lbs, based on the power and speeds you report.
ASIDE: generally the price of an outboard engine is in proportion to its horsepower. I would consider if the 4-MPH anticipated increase in absolute best top speed will be worth what I would expect will be an increase in cost for the 300-HP compared to the 250-HP engine. Unless you are habitually running the boat at full-throttle, the amount of time spent at either 44-MPH or 48-MPH is probably only a small portion of the total time underway, maybe less than 5-percent if your use is typical.
Another consideration: to realize the added 4-MPH you may have to optimize the propeller for the 300-HP engine. Buying a new stainless steel propeller is going to cost an additional $600, so add that cost to the engine cost for the extra 50-HP you will be getting.