That's about 30% of your oil bill right there. Every time you turn your heating/AC unit on, you're actually throwing that conditioned air right out of your home through the roof. Sheet rock is not airtight, nor is it highly insulated. I believe the R-Value averages to about 3, which means it takes 3 hours for the heat in your home to go through it, into your attic, and out of your home. You've probably never seen a large accumulation of snow on your roof and have large icicles each year on the edge. That's due to the snow being melted off and running down the roof to form stalactites. Attics should normally be air-sealed and insulated to an R-value of 38-50.
Never assume the walls are insulated. The only way to know for sure is to poke a hole in one and use a wire coat hanger to probe the cavity. What I've found is that walls normally do have some fiberglass batt insulation in them, but, depending on how long ago it was installed and if it was installed properly, that insulation is not making contact with the pressure boundary (the actual wall). This means that conditioned air is bleeding into the walls through the sheet rock and taking that heated/cooled air out of your house. You'd also have to air-seal the top and bottom of the wall cavities (in the crawlspace and attic) so the air won't be able to move and take heat and A/C with it. I normally recommend dense-packing the walls with blown-in cellulose insulation which air-seals each wall cavity and insulates it to an R-value of at least 11-14.
If the insulation on the walls is sub-standard or not making contact with the pressure boundary, every time you turn on your heater, the heat is bleeding into the wall cavities and out of your home. Also, your crawlspace is probably not air-sealed. If the floor in each room is cold in the winter even with the heat on, now you know why. Insulation would help, but it needs to be in-contact with the actual flooring to do its job. Another way to insulate a crawlspace is to install insulation along the perimeter walls rather than against the floor. This is known as 'bringing the crawlspace inside'. This is done when there are heating ducts/pipes that run through crawlspaces that are already reasonably air-tight. This ensures that heat that bleeds out of the ducts/pipes actually stays in the conditioned space of the home rather than being lost to the outside. If you want to know if this is happening in your crawlspace, just put a thermometer in the crawlspace while the heat is running and check it after about 20 minutes. If the temperature in the crawlspace is more than 10 degrees warmer than the outside, that's where some of your heat is going. The alternative is to air-seal and insulate the ducts/heating pipes in the crawlspace which is labor-intensive. New boilers usually run about $5 - $8k. New windows are a waste of money unless they are in such bad condition that you basically have holes in the walls rather than windows.
Does every room with a baseboard unit have it's own thermostat? If not, you might want to consider upgrading your system. This is a low-cost heating system upgrade which installs zone-valves on the main lines of your boiler to individually control the temperature in each room. Makes no sense to heat a room to 65 degrees if no one is in it. If your boiler is older than 20 years, you'd benefit immensely from a new one. 20+ year old systems are usually less than 70% efficient, which means for every dollar you spend on oil, $.30 of each one is being lost due to inefficient combustion rather than heating your home. Recessed lighting is a notorious energy-loss. Each recessed light acts like a small chimney in your ceiling and allows heat/AC to escape into the attic or ceiling cavity. Newer recessed lights are air-sealed and insulated to cut-down on this problem, but many times aren't installed correctly and may cause fires. Depending on how many people live in your home, you might be better off going with a combination boiler/water heater rather than a separate water tank. I normally recommend units like this if the home has less than 5 people:
Unless someone is living in the garage, remove that baseboard unit.
There is only one way to know if the air-sealing you've done is actually sufficient and that's by doing a blower-door test:
I'll add that all these tactics would also help to keep your home cool in the summer. Do NOT invest in AC until you air-seal and properly insulate your home or your electric bill will be astronomical.
As a rough estimate purely based on the dimensions and existing equipment/issues you've posted, I'd say about $9 - 11k would lower your bills about 25% - 40%. This includes a new boiler, professional air-sealing and insulation of the attic (walls if necessary) and crawlspace.
I'm going to have to do things in step got quotes to insulate crawl space and attic and each range from 2k-4k(2k being regular insulation 4k being the blown insulation) just got an electric water heater so that'll help a little with the oil. I have to look into that sealant checker...but I do know the crawl space and attic have to get done, crawl space first since it's under the rooms in spend the most time in and it's open set up