Don't let sailing dog bum you out. He just loves to tell people that they need to spend more money. It's not true. Don't believe it! Replace your standing rigging with galvanized wire, hand spliced eyes, and industrial turnbuckles/shackles/thimbles. You can replace all of your standing rigging this way for well under $500. Just because it is ugly does not mean it is not seaworthy. In fact, galvanized rigging is stronger than 316 stainless for the same weight aloft, and it starts to rust around the same time you should replace stainless bits due to crevice corrosion and stress cycling. You could also replace your standing rigging with synthetic for less than the price of 316, especially if you can come up with a novel solution for termination. It will be light and cheap, and plenty strong, but UV is a long term concern. It will take years, not months, for UV to kill dynex dux. I imagine you could make your own deadeyes out of aluminum or HDPE for peanuts.
You want enough sails so that you can sail in any conditions, and lose an entire set of sails, and still sail in any conditions. This probably means working sails, light air sails, and storm sails. A full set of each.
Make sure the boat doesn't let water in, anywhere, dump water relentlessly from every angle, spray a hose at your hatches from every angle, throw buckets of water at your main hatch and boards. Any leaks? Much easier to fix now, than out in the ocean when all your bedding is soaked.
To cross the ocean you will need a wind vane, or at least some kind of self steering.
Crossing oceans is infinitely safer with a crew of 2 than with a crew of one.
Bring a lot of food, bring extra food, bring food that can't go bad. Bring fishing gear, and fishing experience.
Bring water, bring extra water. If seawater gets in your freshwater tank, what are you going to drink?
Make sure that the rig is set up in a way that if any one piece fails, the stick stays up. If you are running and the backstay parts, what happens? If you are on a broad reach and your windward cap shroud parts, what happens?
This means more stays, they will add windage, weight aloft, and look ugly and slow you down, but they are nice to have when your backstay turnbuckle goes zinging up over the cockpit.
Make sure the rudder is sound, and that you have an emergency rudder. (windvane?)
Bring storm survival materials. Series drogue, para anchor, storm sails, etc.
Bring materials to fix your hull in an emergency. Collision mat, splash zone, etc.
Watertight bulkheads and watertight lockers are not convenient, and do not offer good ventilation, but they could save your life.
Bring an EPIRB. Bring signaling materials. I suggest a radio as well.
Have a way to navigate, and a backup.
Have a way to do anything critical even if something fails.
I would take the inboard out and toss it. Put on a little outboard in it's place. The inboard is going to cost more to replace than the boat is worth. It should be new if you want to cross the ocean with it. One outboard, and a small backup 2-stroke will serve the same purpose, weigh less, cost less to maintain, and be easier to work on. So what if your boat will motor slow. It's a sailboat, not a motorboat.
You can achieve all of these things quite cheaply if you are ingenious and have a lot of time on your hands. You don't need a chartplotter and an inboard and a generator and pressure water and TV and laptops and all that to cross an ocean. You need a sound hull, a sound rig, backup plans for everything, and a smart captain.
It's really safer than driving to the marina, so don't get discouraged.