I think it doesn't matter when you start.... in spring you wrestle with flush, summer with shearing and flies, autumn with fluke and winter with frozen water and feed prices. And this year, all year, whatever the season, we have been dealing with scald.
I say get 'em in, enjoy them, have fun, learn loads and with a years learning behind you, put them to the tup!
As for land... you will probably need to add hay and licks. I had 3 ewes originally on 1 acre and 1/2 acre paddocks and rotated. In summer I had too much, in winter I was supplement feeding. If you had primitives i.e Soays, Shetlands etc you may scrape through depending on how early grass comes through in Spring/weather but with greedy fat commercials (I have Texel x's and Lleyn x's so I know how much they munch

) you will struggle over winter.
My 13 lambs (aged 7 months) stripped a 1 acre field bare in 3 weeks! Greedy beggars!