Should I try to start it
I'm pretty sure I'd be tempted to "see how it runs." If you are just going to do a brief fire for 30 seconds don't worry about cooling. Depending on "your best guess" (look at the dipstick) I might be tempted to not change the oil. Pull the plug loose enough, that with a glove on, you can drain a sample right out of the bottom. This will not only give you an idea of what the oil looks like, but if there is any/ much water in the pan.
I would follow with pulling the plugs and squirt oil or atf in the cylinders. Bump the engine to distribute the oil, let it sit for awhile. Light oil as opposed to heavier. You want it to penetrate. You might mix a big of diesel in to thin it or even a small amount of gasoline, same reason. Maybe 2 parts gas to 8 oil. You just want to thin it a bit
After it soaks awhile, several hours, get the battery in get it to crank, and spin it around a bit to expel oil. At that time you can determine if it has spark
You may or may not be able to get the carb to even work, so you may have to prime a bit of fuel into the throats directly. You can try filling the carb with a syringe/ squeeze bulb.
Disconnect the tank fuel line and either cap it or direct it into a safe container with hose.
If you have "enough stuff" you might try a siphon can from above, connected to carb inlet.
When I was about 27 my dad bought a junk Case tractor. It had sat for at least 25 years with the exhaust elbow "up." But it had a drain hole at the bottom of the el. Amazingly the cylinders were clean as a whistle. We ended up doing a valve job, but for fire up to "see what we had" it required a working magneto and squirting fuel into the missing carb manifold. This is it after Dad painted it the year after we got it "tuned up"
On a side note, LOL those fenders could be a problem........you "can't see." After Dad got it running he was plowing one field. The thing started to get stuck, but what was really happening is that a tube had failed. The thing walked the wheel right out of the tire before Dad realized what "it was doing!!"