Reminds me of some of the struggle I had with my $50 neglected 1979 Toyota 4X4 pickup. At least one hole for an ex man bolt was stripped and I tapped it out to a larger inch-based diameter. Seems unlikely the steel bolt would be damaged; the aluminum alloy head would be area where damage occurs.
Not starting: explain what happens and what doesn’t happen when you turn the key to Start.
The water could be an indication of a blown head gasket. It could also mean there is a cracked cylinder or head. You need to check for spark and check the condition of plugs for clues to the “crime”. Check to see if fuel is getting to the plugs. If all that checks out you may then want to check the cylinder pressures.
I have an '87 that works as well as new. Age is no reason to ditch this car, if that’s what you want to drive. The water pump busted a seal on mine 15 years ago. Replacing it was easy and cheap. That doesn’t sound like your problem though.