1 and 5) For me, I just knew. I got on some bikes and I HATED them. I talked to the LBS guys about what I didn't like (too twitchy, too small/cramped, whatever). Then they had me ride other bikes to compare the ride. I found that in one manufacturer, I had to go way out of my price range to find the "ride" I enjoyed. With another, I got on the bike and thought, this is it. Then it came down to 2 similar models within the same brand. Ultimately, slightly better components and a less aggressive geometry won. I could still make the fit a lot more aggressive with the stem angle and headset down the road, which I did after about a month or so and then again about once a year for the next couple of years. Try to pinpoint what the differences are that your feeling and qualify them.
2) See if you can take some longer test rides. In the US, you can often just give the shop your license and credit card and hit the road for a bit. Try to differentiate component performance (shifting and braking, primarily) with geometry / frame material and performance (responsiveness to accelerations, responsiveness or smoothness in cornering, smoothness climbing and/or descending). You probably won't get a favorite of either, but you can weed out the bad (shifting horrible, gear range difficult / too easy, braking hard).
3) You probably don't need detailed measurements done. A lot of sizing has to do with your flexibility. You may have shortish arms or a short torso, but how flexible is your lower back? How far forward should you have the saddle because of your femur length? Any of that can affect your functional reach to the bars. With so many compact geometry frames, seat tube height and standover height becomes less important. Then it comes down to how much seat post would you have exposed on size X. Would that mean the bars are very low compared to the saddle? Can you handle that? If no, then maybe you should see if you can go up a size.
4) You can get a good carbon bike for 2k. It probably won't have super wheels or top notch components, but the feel of the carbon ride might be enough to persuade you to stick with it. BTW, don't worry about breaking the frame. Yes, you need to be careful about overtightening parts (on all frames) and taking care of it, but if you fall, particularly at 0 speed while learning to use clipless, odds are you aren't going to break the frame. If you do, then you probably fell on a curb, and your ti or aluminum bike could also be trashed. However, one caveat is that no matter which frame material, you get, it's good to have a replaceable derailleur hangar. These things can get knocked off our out of alignment fairly easily when the bike is dropped or banged around. Not being able to fix it means your entire frame is trashed.
Back to the choices.. Titanium is going to be in a similar price range to carbon. I don't have enough experience with ti, but I think you'll find fewer bike models made with it than carbon or aluminum, so it could just come down to whether you like the selection. There are a lot of good aluminum bikes out there, though for race quality bikes, most manufacturers have moved away from aluminum. Cannondale and Cervelo still make a good quality race bike in all aluminum (CAAD9, S1). I say that because you can still get some nice components for your 2k budget on an aluminum Cannondale that no longer comes stock on an aluminum Trek, Specialized, Giant, etc. Because the frames are cheaper, these will be better components than on a $2k carbon bike. Plus, these frames are probably stiffer than the entry level carbon.
Finally, it's probably not in your budget, but it could be for used.... The main issue with flying with the bike will be packing it in a bike box. So, bikes with seat MASTS (not removable seat posts) are not a good idea, because they may not fit in the box. Also, if your fit changes over time, which it probably will, then once you cut a seat mast you are stuck with that height.




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