Hi Matt, I reckon first order of business should be joining your friend's astronomy club. Observing with mates increases the joy of the hobby ten-fold (unless you end up being an imager – reclusive curmudgeons those...
)
Once you get out under the stars with a bunch of likeminded people you will gain a much better perspective of sizes, views, weights, setup times, cost, etc. I wouldn't rush into any purchases before sampling a good variety of scopes. At those astro club gatherings (formal or informal) people will almost invariably be happy to share their scopes with eager newcomers (a big part of amateur astronomy is equipment pride), so don't be shy to ask.
Cheers
Steffen.