you'll get lots & lots of answers. these are my personal views, and you'll have to think them all through for yourself, too, and decide on your personal views.
1) you ditch weights at the surface if you're in trouble and can't stay buoyant, like maybe suddenly there's bad waves and spray and you need to be higher out of the water to not get smacked and so the boat can see you better. you need to ditch weights underwater if you're at the 'better bent than dead' crossroads and plan on hustling up, calling dan, and going for a chamber ride. my personal views lead me to not worry about ditchable weight. i usually use ankle weights in my crotch strap - technically ditchable but out of my way.
2) practice. keep track of what you're wearing (more neoprene takes more weight to sink it), what tank you're using (different tanks weigh different and swing different), and how much weight you needed for the dive in your log. soon, you'll be able to judge and guesstimate pretty close based on your past experiences. there are lots of threads about the 'tank with 500 psi' weight figuring method, and that is the gold standard, but unless you then do every dive in exactly the same suit with the same type tank, you need to re-figure with a low tank again every time something changes. *or* give it a good guess based on what you have written down in your log!
have a great day!