Difference in fishing from Skiff, Flats, and Bay

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Could I fish 3-4 comfortably from 17-18 ft

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Not happening if you are doing a lot of casting. Also not much room in that size range for rods and gear for 4 anglers. 3 would be doable. You would need to limit how many rods each person would carry and likely just have everyone fish out of one tackle box.

Unless you are looking to start fishing in less than a foot and utilizing a push pole then I don't see the benefit of a flats skiff over a 19ft bay boat.

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family boat.

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What's you're idea of a family boat? Just need ample seating? Looking for creature comforts? Some type of cabin?

I got two.

My nephew and I bought our tracker Grizzly’s with trailers new a few months before Covid-19. I think he may have paid $7,200 new and I paid $8,500 (boat, trailer, engine, reconditioned trollmotor).

My 1648 tracker Grizzly nothing in it with 40 hp tiller. It tight with two people but works.
Rigged it out with running lights, electronics, stereo, and 24 v trollmotor. Simple and easy to clean. Fish Pearl, chef pass, spillway, marshes South of Houma, Okissha, oxbow lakes, and False River.

Nephew has the Grizzly 1448 with 25 hp Mercury. Two people can fish it, but it is tight. He fished alone more. One person it is a pretty sweet boat for marshes and HP restricted areas like Lacassine. We rigged it out with bildge, lights, electronics, and interior night lights. We rigged it where it works well if two people fish out of it. We hauled some nice bass and reds in his boat. It simple and easy to clean. We been using it more as the 25 hp Mercury does not burn much gas. I think that 2019 Mercury after one trip around 35 miles running at Toledo Bend burnt 3 gallons of gas.
Not fast but it works.

I also have a bigger crestliner aluminum boat I keep at my camp Toledo Bend. I use it more to fish with family or guest.

Look at the hybrid bay boats, they may be above your budget but seem the best of both worlds.

Have you looked into panga style boats? Long and skinny with lower horsepower. Can get skinny plus handle some bigger water. You can get into a new 26’ with engine for probably 30-40k. Would be utilitarian but have the size at least.

I wouldn't do it OP, personally. Its one thing if you know exactly what type of specific fishing boat you want, or you just want say a 14 flat boat.

In your situation with the details you've listed, I'd just try and find a boat that can do it all with.

Some things to keep in mind with multiple boats is you have multiple registrations, multiple insurance potentially, multiple motors to service, and multiple boats to store.