I hear ya. The worlds changed a lot since you spent your $165. I’ll keep repairing and fixing the set up I have now.
Any tips to solve “the worst setup you’ve ever seen” would be appreciated. I’m here to learn.
Actually, nothing has changed. It's all the same except for the cost due to inflation. Back in my day a used boat like I had would cost about a grand. I did it for half that. New boats were in the $2000 range. Cheaper used boats boats could be had, just like today, but many were not serviceable, or the cost to make them usable exceeded the value.
Your boat is too far forward. If properly positioned the bunks could possible be OK. Since the trailer is not ideal, if you put the boat in the right place you might need to move the axle to get the proper balance. You need to make the thing right to know.
Does the boat have a bow eye? If not, it's not intended to be a trailer boat. The winch is set too high. Is that because of no bow eye and it's now set to winch it up on a cleat? (baddddd idea)
Surely, the winch post has no stop. Easy peasy and just a couplabucks. Pictures are not complete and could be deceiving. Looks like the stem is too low. No front trailer roller? If not, that's a cheap option as well.
As we all know, bow tiedowns and transom tiedowns are necessary. Not just a good idea but a legal requirement in most states. Don't put the boat on the highway until you get them.
Who is the manufacturer of the motor? Obviously repainted. Why? You need to provide a serial number and model number so we can help you get parts. Regardless, you also need to know the oil:gas mixture. Even if it runs great, parts will always be needed in the future. Before you ever run it, the water pump will absolutely need to be replaced, gear oil changed, spark plugs, etc.
Good luck. Forget about painting until you figure out what other expenses you need to make.