We have a 1986 T37 and love her, but she is a lot of work. On older models, the inside of the bulwark is hollow so if your sailing inheavy winds or if it's just raining the water
can run under the cap rail and get inside the bulwark. From there it can run down the length of the boat and eventually finds its way inside making it difficult to stop leaks
. This can also lead to chain plate
problems and coring rot. In the later models they realized this designs flaw and foam filled the space and sealed the cap rail on better.
I'm not sure of the older models and the weather helm, but our boat we find we will reef at about 15 to 18kts of wind
and that will greatly reduce the weather helm. From there she will sail herself depending on point of sail.
Like others have said, check standing rigging
, bow spirt, bob stay and the water line fitting, check all thru hull
seacock valves, cuttless bearing by shaking the prop shaft from side to side and same thing with the rudder
. If the boat has batteries in it make sure all light and electronics
Overall the T37 is a great boat if she has been kept up. We looked for about two years to find our boat. When we first started our budget
was around the same as your, but as we educated our selves more and looked at a lot of boats we realized that most of these boat needed a couple years or work and a lot of additional money
. So we opted to spending more on the initial cost of the boat so we're just not bogged down with projects. Your views might be different and doing projects is the fastest way to learn the systems on your boat. Best of luck.