I just recently went through the repower process on my 2004 228. I went from a 2004 F225 mechanical to a new 2023 F250, fly by wire. The new F250 weighs in at 551 lbs. The conversion to fbw was well worth it. Running the motor is like a video game, there is no effort whatsoever. It handles the boat effortlessly. I played the waiting game with Yamaha for 2 years to get one, so I understand the availability issue. Many times, I considered switching manufacturers, and going with Mercury or Suzuki, but I had no real reason to switch. My old F225 was, and stil is, running, so I had the time to wait. My repower was a want to, not a have to situation. I purchased all my conversion rigging early on, thinking when I ordered my motor, it would be here in a few months, so I had plenty of time to recover from the investment, which was a little over $2K, just for the rigging, still worth it IMO.
Are the prices you're getting MSRP pricing? Are you getting pricing from your dealer, or are you just a random caller off the street, price checking dealerships that you have no relationship with? I can tell you that I paid well under your $27K price for my Yamaha F250, which came with a 5 year warranty also,, I luckily hit a Yamaha promotional campaign. I've had a relationship with my dealer for 14 years, and that's a long distance relationship at that. I'm in Kentucky and they are in South Carolina, and the price I paid, I feel, reflects my dedication to them as my dealer.
In today's world of continuing supply chain issues, which manufacturers still claim is Covid related, it's pretty much gone to a supply and demand environment. Prices are inflated from where they once were, and our society of instant gratification, is paying the inflated prices, so some dealers see no reason to cut you a deal, especially if you walk in off the street.
Stick it out and get what you want, don't just settle for whatever is out there. If your motor still runs, you're ahead of the game and have time to wait. And I can tell you, with me having a 228, you'll be happier with a 250 hanging back there than a 225. The 225 will get the job done, been running mine for the past 7 years with one, but with my new F250, I have a brand new boat.
Good luck.