Welcome to SBO.
As observed by
@dlochner concern about the location of gel cracks under the mast step is
at least a 4 out of 5.
As
@Don S/V ILLusion mentions the gel cracks on the surface leads to an inspection of the structure underneath. Gel Coat serves as the water barrier between the inside and outside of the boat. The boat primary purpose is to "Keep the Water outside of the boat".
I suspect it will be a "Pair of Kids in a Candy Boat yard". It would be a idea to take
@Scott T-Bird up on his offer. I am certain when you head home you will either have found your boat or have a great knowledge about how to look for the boat.
Looking at the additional pictures, I would conjecture:
- the 27 leads me to believe the boat was used in a fleet of rentals. Either a youth program or a lake boat rental operation.
- the design of the hand rails would lead me to inspect how they are secured to the deck. I appears there is a screw or bolt running down from the top into the square base. This would be a path for water to get into the square block of wood or if through bolted into the cabin and or deck core. This would contribute to moisture destruction of the core and soft decks.
- The standing rigging (what can be seen) does not raise any red flags. This is another critical area. The way it connects to the mast and the deck are what holds that heavy mast in the air. These are a critical inspection area.
- @Timm R Oday25 explained about his boats issue with the "chainplate" connection in the boat. The critical point raised was his experience with wood rot. On these older boats it is a natural occurrence brought on by maintenance neglect or deferral.
- Sails are the engine power to your boat. They will cost more than a new outboard. Budget in new sails as there is a likelihood the ones on the boat are more blown out than grandma's bloomers.
Older boats can be a path into boat ownership and sailing experience. Like buying a wrecked car and rebuilding it. There will be expense and frustration. They are never an investment that will fund you retirement. They can bring a whole lot of fun to your life.
Come to some solid (perhaps even written down) agreement with your friend about the boat. The planned use and share of expenses. Good friends are more difficult to find than boats. Don't let a boat partnership get in the way of your friendship.
Have fun. Sailing is a great way to enjoy the water.