The 52cm raleigh with Brooks at $225 is the best buy, beyond maybe that Mixte Miyata, imho. At 5'9 you're probably going to be better off with the 52cm than the 50cm.

I'm 6'0 and ride a 56cm.

Bonus on the Raleigh is that you're getting a $120 saddle out of the deal, and it doesn't look like a total piece of crap. Raleigh is still a decent commuter bike company.

That is an original Raleigh too. Needs a new chain, and probably could use some kool stop pads on the brakes. Neither is going to bust your bank, but you're still going to end up having to buy them and install. I'd personally recommend taking that bike, going to your LBS and having them put on the chain, and brake pads. Get to know them and make friends early. As things need replacing, let them explain to you what are the best options. Velo Orange sells a lot of parts that would work well on that bike, and you could go to someone like universal bicycles (google it) and find a quality rear rack for under $45 shipped. Tires on 27s are limited, but I picked up 2 sets on my araya for under $40 total (not in one shot).

The brakes are center pulls, look like they're original so the only other "new" part I would worry about in the near future is probably cables. Once again, something you'll find easier to get with the knowledge and friendship of the LBS.