Mixx, I'm sure you'll have no problem with the ladies in Montreal, 2 months in the summer will be awesome! I'm not too sure about on-line sites, POF doesn't seem to yield much, mostly Anglo chicks and you don't want to be fucking with square heads in mtl, go for the Franco Quebecois pussy! One site that was really popular with people in Quebec when I lived there a few years ago was
http://www.doyoulookgood.com it still exists, its in french but you can switch to English (upper right hand corner). Check it out, if you need help writing a profile "en francais" let me know!
PDX, to answer your questions:
1) Candelaria is a very cool area, I've only been there twice so don't know it too well, but from what I saw it nice; interesting architecture (its the oldest part of the city), great bars, pubs and restaurants, etc. Very walkable, everything you need is close and theres lots of people about. You should be able to find cheap accommodations easily, however, this area can be a bit dodgy at night and even the day. A friend from school had his camera jacked by a thug during the day on a back street, from what I've read online, this sort of things happens quite a bit.
I personally don't like the Zone Rosa and Parque 93 areas much, they are a bit too posh for my liking but I went to both areas for some drinks and grub and they are quite nice, with North American prices. There are some REALLY nice bars and restos in these areas, Zona Tee gets very packed on weekend nights. This is actually a good spot for Gringos with limited Spanish to hang out, you'll meet lots of Colombians who speak English here, GOL really liked this area and did alright there with the ladies.
I'm staying in an area called Chapinero, its pretty cool. Its between Candelaria and Zona Rosa, I like it a lot, tons of decent little bars and pubs and theres a lot of young uni students in the area. It also happens to be the LGBT area of Bogota, so that may put some people off.
I suggest staying in an apartment like I am, some hotels don't allow guests after 22:00, as GOL found out! PM me if you want to stay in the place I'm in, its $55 USD/night or around $750/month ($150DD). Props again to Mixx for suggesting the website where I found the place.
2) I haven't gone out alone at night, just out a couple of times with GOL and some guys from school. All the stuff they say on here and in Roosh's book "Bang Colombia" is 100% true, its tough to pick up from bars, theres lots of cockblocking but, especially if your Spanish is decent, you can get #'s and set up dates easily.
3) I haven't done any day game yet but I'm getting there with the Spanish so, I'll be trying that soon enough. I've been relying solely on pipelining via internet (Colombian Cupid, Tagged) it was frustrating at first due to flaking but I've have had a couple dates so far and its been good. My game level is intermediate, nothing special but I can pull, Colombian girls are sweet but not very slutty like home, they take work! The one I did bang lived in the UK fro 3 years so she spoke English very well.
4) People dress very smart here, way better than me, that is something I have to improve on and I look forward to doing so. I'm gonna be getting some custom made threads here in the next week or so, there TONNES of tailors in the city, even one that makes custom bullet proof suits:
http://miguelcaballero.com/cms/front_content.php
As far as how they dress, well its cool here temperature-wise about 15-20 (nice and warm for me, I wear tee shirts!), so people are wearing sweaters, light coats, scarfs, etc. I don't know how to describe the styles, a bit bohemian (a bit hipster-ish but nothing to wack like in NA), solid colours, some of the pics posted in the recent fashion related threads on this forum seem about right. You won't go wrong by dressing up, trust me, especially in Zona Rosa, people dress to impress and wear expensive clothing.
I'd suggest even bringing an empty suit case and shopping here; Bogota made leather dress shoes for $30-50, FINE custom suits for $250-400, custom made jeans, dress shirts for $25-40, etc.
Hope that answers your questions!