Hello everyone!
I live in Portland, Or and recently purchased an SC Draft Lite. I need to bike the 3 miles to school, and bike around the city as I do caregiving for people with disabilities. Low-cost, low-maintenance.

I had the bike five days before someone sliced the lock, and stole the bike outside someone's house I was providing care for. I'm heartbroken, and broke!

All this being said, I need your advice on a roadbike for myself.

My question is 2-fold:
1) I need a single-speed, roadbike,under $300. what bike do you recommend, and where should I get it?

2) I need a U-Lock that the most determined thief wouldn't bother with. Stolen bikes is pandemic in PDX.

I make minimum-wage, so don't bother recommending me a bike that's over $300.

Bikes I'm possibly looking at:
Motobecane Messenger
Nashbar Hounder
A single-speed Micargi?

ps. Or you could just give me that dusty one you never ride anymore. Do it for love. Do it for charity. Do it for the children.

Hit look for something used, at a bike CoOp, rebuilt by them .
https://www.citybikes.coop/
https://www.communitycyclingcenter.org/
of course many more retail shops have some used bikes..

Yes you probably need a U lock and some heavy chain, hardened links of square steel.
the U lock to serve as a Padlock

The Micargi RD818 states that it is not available in the US so you'd have to look for another.

If you are providing the caregiving, if you spoke with them about your stolen bike, might they be willing to allow you to lock your bike inside?

Thanks! I was actually disappointed at how expensive these "used" bikes were. Even the "as is" (missing pedals, brakes, etc) were pretty expensive. Bikes (even old ones) go for a premium here. I think I'm going to go with a new one, b/c it's only a few dollars more.

Why a single speed road bike?

Schwinn Single
Windsor Clockwork

Because in PDX it makes good sense. It's mostly flat, it's low maintenance for the crap PNW weather, and (with the exception of shiny new ones, apparently) they're a lower theft item.

My ss roadie commuter is a dumpster salvage. I built the wheelset for $100, and put maybe another $100 in parts into it. Most of it was spare bits and pieces I had around.

Why ride a single speed? Reliability is about it. Plus, it's not very hilly around me, so no need for extra-complicated gears. Plus, I'm a raging hipster. I keed! I keed!

That Windsor Clockwork looks pretty amazing...

Get a reliable beater for 30-80 bucks, if the paint/bike looks real nice, add some spray paint and scuff up some stuff! Definitely get the u-lock anyways.

Here's an example of a bike for sale in PDX: https://portland.craigslist.org/mlt/bik/2598589176.html

Crazy expensive for a mid-level bike, that's almost 30 years old. Why NOT buy something brand new for 30 bucks more?

Difference in quality of workmanship?

seems to be a PDX and college towns in general thing , used bike price bubble.

What happens to all these stolen bikes?

I've been told they're taken south (like WAY south) to LA/San Diego and sold off either together or in pieces.

Go with a Ulock and hardened steel chain combo. Just the locks are probably going to weigh around 12lbs, but if bike theft is as out of control as you make it sound, it might be a necessary evil.

Nashbar.com and bikesdirect.com both have pretty good bikes that wont break the bank.

If yer looking for a SS or fixed-gear bike, you might have luck re-posting in the SS/FG section.
Singlespeed & Fixed Gear

Someone might even have an old beater kicking around for you to buy....

My son has a Hounder (wanted cheap, single-speed bike for college and we had not been able to catch any deals on CL). It is heavy but isn't a bad bike. I serviced the hubs (a bit spotty on grease and a few metal shavings that might have found there way into the wrong place); removed the freewheel and fixed cog, greased the threads and reinstalled; didn't like the feel of the BB so I picked up a UN54 for < $18 on Amazon and swapped that out; removed, lubed and reinstalled all hardware; and swapped the tires with some kevlar-belted ones from Performance ($10 on sale). Wheels came reasonable true. Riser bar and stem are steel (heavy but should hold up to anything), seat post is steel, brakes are single pivot but work well. Rides pretty nice and I'm sending it down to him with his room mate this evening so we'll see how it does in the real world.