tsl

I know exactly how that goes. When I bought my Trek Portland in 2007, even as a leftover 2006 model, it was far more than I should have spent. (It was about 10% of my annual salary.) However, it was exactly the bike I needed, and after the test ride, I couldn't not have it.

I put it on layaway, and paid as much as I could as often as I could. I'd wanted to have it within four months. The Fates intervened, and between that and eating a lot of ramen noodles, I had it within two. I've not looked back. Every ride is a pleasure, and six years later, it remains the one bike I'd keep if I could own only one.

So remember, layaway is an option and you've got four months until spring. That's about $40 a week. I found it was a lot easier to make payments on something where I'd already put down a deposit, rather than stuff it in the piggy bank--less temptation. Plus, it kept the bike reserved for me.

As for your routing, really the only question is which way to choose to get to East River Rd. Or that bike path to RIT. I've never used it becasue I've never needed to go there, and it looks better suited to hybrids rather than my roadies.

Anyway, I'm not fond of Joseph Ave. Ford St is okay. You can take it all the way to the Riverway, although the bridge can be congested at certain times, so you might want to start on the west bank before crossing to the east bank in UR. Alternatively, turn on to Plymouth at the roundabout. Plymouth is really low traffic and well paved.

I really like Genesee St since they repaved it and painted sharrows on it this past summer. It made a huge difference in how I'm treated in traffic. I use it daily from Arnett Blvd to Brooks Landing. From your neighborhood, I'd use Brown St to get there rather than West Main.

Standalone 

Buy *and* start now. If you start in the cold weather-- even one day/week -- you'll always know that you can do it in any weather. I started commuting in the winter, and (despite some work and grad school related lulls) it has become a permanent part of how I get to work. On any day that my school district is not cancelled, I can never really say to myself "well, you've never been out in anything this bad...." Hard downpour/driving rain, blizzard, and gusts over 40 are my usual cutoffs, and I have been good down to 14f on 7 mile rides to church choir.

Rhodabike

I've gotten my best last-years-model-on-sale bargains in January. Christmas is over, so no-one is buying bikes as gifts, but spring is still a long way off. The shop employees practically fall over themselves to sell someone a bike in January - unless the shop also has winter gear such as cross-country skis. Then they are a little less worried about making a sale.
Only you can decide whether you really want to start now or not. If you have ice to deal with, that may mean studded tires, and lights are usually needed as well. Winter commuting isn't for everyone. Perhaps try a ride on a Sunday morning in the winter to see if you can deal with the conditions in broad daylight, first. I commute in winter, but I personally don't recommend it for someone just starting out.

rumrunn6

route sounds awesome and here's my vote for the trek FX series, you should be able to find a decent used one on CL, I bought 3 over the years, 2 just last year for family members. JUST GET THE RIGHT SIZE that bike come in many frame sizes.

rumrunn6

wutz your location?

https://southcoast.craigslist.org/bik/4187192697.html
https://boston.craigslist.org/gbs/bik/4197128392.html
https://boston.craigslist.org/sob/bik/4197668599.html
https://boston.craigslist.org/gbs/bik/4198188237.html
https://boston.craigslist.org/gbs/bik/4206407628.html
https://boston.craigslist.org/gbs/bik/4204203486.html

Notgrownup

I was just looking for giggles and saw Tryon bike shop and they sell KHS... for a little over $400 you can get a KHS Urban X, fenders and a rear rack...Looks like it would be a decent starter bike that wouldn't break the bank... https://khsbicycles.com/bikes/2014-khs-models/x-14/
I had a Cannondale Quick 5 and it rode good... i only kept it for a month because i really wanted a road bike...I like the idea of a Hybrid but find myself way more comfortable on a Road bike..Funnnny...Start to shop now...the deals are everywhere and take your time...Write stuff down , waht you like, dislike, Rim or disk break, Hybrid or road, fenders or not..etc...

tsl

Jeepers. I forget about Tryon. They're more into MTBs and I'm a roadie. But I started going there after meeting one of the owners on a charity ride this summer.

They're on North Winton between University and Blossom across from the Tops grocery store. They have a little different business model than most bike shops and may be more willing to dicker. Plus the shop is very small. Not much room for bikes on display, maybe a half-dozen last time I went there. But also, there's little incentive to sell what's on the floor and a greater incentive to order the right bike.

There are several bikes in the KHS urban line that are worth considering. Of course, as a roadie, the Xtreme caught my eye. The rear disc brake caliper is even in the right place.

john426

I would start looking now. Not only can you get unhurried service from a bike shop if you are buying new, you also can pick up a used bike really cheaply. It seems like prices go up and selection goes down when buying from a private party in the spring. John

Stryver

Check out the local co-op. https://www.rcommunitybikes.net/ Show up, do some volunteering, ask some advice, see what they offer. There is a very good chance you can get a good commuting bike (and the skills to maintain it) in exchange for your volunteer time, and now is a great time to start volunteering, you don't need a bike yet, and they probably need an extra pair of hands. You'll also find a group of people excited about biking to keep you motivated for your commute.

Barring that, my recommendation is to buy used from a local bike shop, particularly one that would let you trade-up later. The first bike you start riding on is the one that will teach you the most about what you like and don't like in a bike. If it ends up matching what you like, that's wonderful! If not, you'll want to be able to get a different one. You are very likely to desire to modify the bike (different saddle, tires, maybe pedals, carrying devices, pedals, lights, etc.).

I don't recommend preparing for occasional commuting by getting a trainer and riding indoors over the winter. While it can be a very good workout, it takes a certain amount of dedication that riding outdoors doesn't, and can result in burnout before you ever get started. If you are very motivated for riding for fitness, look into it.