Use the scrap trick to get size as needed, but watch your performance. You don't want to drag it down too much or crash (should only happen if you run out of memory). I use console commands to boost my settlement size, but that takes a bit more work and won't work on consoles. I haven't had any slowdowns or issues so far, even with huge builds, but I've got memory to spare and a decent machine.
Definitely the biggest by far and you can unlock it as soon as you're able to reach it and clear the mirelurk infestation (ie, kill a queen, a few kings, and lots of normalish mirelurks). It would be a rough match very early on, but easy once you have a combat shotgun. Doing it before combat shotguns appear would be doable... I'd think frag mines and grenades could get the job done pretty quick. Spectacle Island has the advantage of being very isolated as well, which is great if you're hurting on performance (ie, playing on console or old PC).
Sanctuary is always my #1 since you get it right away, it's huge, tons of scrap, and you can easily incorporate houses and hedges as part of a wall to isolate smaller sections early on before expanding later.
I've been growing fond of The Slog lately. It's got a lot of flat land if you tear out the fences and playground and it's easy to just build atop the central structure. Abernathy Farm has a fair bit of space as well, but their main structure is tricky to build on top of and there is no water source. Nordhagen Beach is a little cramped, but fun location and there is enough space there for a good sized build. Warwick factory place is fun. It has a huge structure to work with. The land is a bit cramped otherwise, but it has excellent innate defensibility. Graygarden is big, but it's almost all on a steep hill with no water source (funny considering the quest to get it)... but you can utilize the highway with some clever construction, although NPC pathing will be an issue at times to get up and down. The lighthouse has a bit of space to work with and a cool theme. Starlight is an excellent choice. Huge area, water (remove the barrels), and good structures to use that don't take up too much of the area.