I would say roll it back a notch , the trs 72c combo isnt a bad set up , i dont see you wakeboarding behind a 87mph boat but your current set up could be a 900hp boat that could still board behind and be reliable. Today you can buy a spare trs and trans for the price of 1 bravo. If your intent on using it for a occasional tow rig put 4 blade bravo 2 props on it build it for torque make it look good k planes if not already equipped and have fun.

I think you answered your own question with your first sentence compared to your initial post. I would get your boat up to snuff to sell because your not keeping it if you have thoughts about another boat. Those thoughts usually turn into a purchase.

Move up, there's no guarantee that the upgrade will be a smooth process and sometimes old parts don't like new power. Agree with everyone about pumping money in a boat that doesn't have much value. Out with the old, in with the newer, plus with this economy you'll never see better values for purchasing.

As stated, I see good points for both sides.

If you update your boat, you know what you have. Peace of mind is worth some $$$, how much is subjective to the boat and owner. $40k might be excessive unless you plan on keeping the boat for a LONG time. Maybe a lower budget upgrade to make sure it is mechanically sound.

If you buy a newer boat, you are always rolling the dice. A survey helps, but it is no guarantee. You could buy a new boat, and have to dump some serious money into it within months. Plenty of threads on here where people did just that.

If you have another boat on your mind, it is time to sell. I had this same debate last year, keep my 311 or sell it and buy a Cafe. My 311 was more or less done, did everything I wanted it to, and was an all around great boat. When I was driving it for the last time taking it to the ramp, I remember thinking what am I doing here, this boat is great. A year later I can tell you I don't regret it a bit. Not only do I love my new boat, but the new owner of my 311 is an OSO member and is making that boat nicer than I was willing to.

No reason to upgrade to Konrads......Unless you are running more then 675HP. TRS are stout, and their are a lot of them lying around for short money. but I still say, sell the boat to someone starting out, and use the money towards a newer more efficient setup. Fall is a great time to buy, spring is a good time to sell. just my 2 cents

We all usually tend to spend money on things that we enjoy and have fun with,---not always because they're the best investment.

A friend of mine has a boat that he has had for 11+ years with about 750 hours on it. Plus, he has it all paid off with the bank now. He wasn't sure if he wanted to upgrade it or just sell and buy something newer, but he really enjoys the boat he has had for all these years. He found the right people in 3 different shops.....for repainting it with a new graphic design, another shop for re-rigging new gauges, and electronics, and other upgrades, and another shop for rebuilding/upgrading the engines. He is having things done the way he wants and likes it, and it will be fun for him to see and feel the difference with the same boat and all the previous "seat time" he has had in it.

I did exactly what you are thinking about doing.... Smart, Dumb or just plain crazy.
I am having to adjust to a few things, but I'm working through them this season.
I have a 89' Fountain 10 meter, had it for 16 years, had the same set up as you... 420's in front of the ever so popular BW trannies and TRS's.
10 years ago had one side go down ( engine ) replaced both engines with newer and better guts. All working great, just maintaining the little stuff !!
Last year blew out the main output bearing on the tranny, no damage to drive. Thought it over and decided on the Konrad Conversion.
Someone performed the conversion and couldn't be happier, gained some speed and I'm hoping reliability. ( not that I had problems with the TRS's, just a bearing )
Did a little paint and cosmetic work, installed a few pieces of vinyl to update the exterior.
Love the boat, know the boat and will keep it until I'm ready to move on.
I knew going in, the money was spent and ill never see again, but that is boating and the cost of having fun.
There are no guarantees in life, enjoy what you have and who your with.

IMO, boating is not an investment, it is a major expense. If you are into personally working on your boat and this is your fun, DIY. If you want mostly a turnkey boat with minor upgrades & repairs, buy an great looking low hours boat with a stock drive/engine package as new as you can afford. With about any 30'+ twin engine sport boat, it is easy to annually spend $10-22k. The best value?....get a golf membership instead of a boat

Keep the old bird. If she is dry and solid, spend some money to keep her.

I'm a guy who "upgraded" for speed and efficiency, now I just miss my 357