Planning the Baltics, Part 3: The Question Spirals

Now that I have my itinerary planned, I can book my hostels/trains/ferries/flights, right?

No, as Boromir would correct you...

No, no, no. It is not simple enough to just say "I need a hostel on such-and-such date. I just find the cheapest option with the best overall rating!" 

You novice! There are so many more complications. Do you think that it would be so simple for a girl who made no less than five itinerary options before booking her flights? Do you?

Here are five. There may or may not have been several more.

Thus, the question spirals begin, with each and every step of my planning process. 

I need a hostel for this night in _____ city!

• Does it have free wifi? 24-hour check-in? Towels/linens included? Free breakfast? Do I need free breakfast? What's in the free breakfast? Do I really want pate for breakfast, even if it's free? 
• Does it have charm? Like "prison converted into a hostel" charm? Or like "riverboat converted into a hostel" charm? How about "firewood storage facility for the royal castle converted into a hostel" charm? Or "Boeing jet converted into a hostel" charm? I think you get the point. 
• Is it the one where all the reviews mention the poorly-designed showers that guarantee your clothes will get wet outside the door?
• Is it in a cool neighborhood? Safe neighborhood? Lively neighborhood? Residential (ew) neighborhood?
• Should I stay at the hostel with the tattoo parlor? It's only my first night, but maybe I'll wanna commemorate the occasion with a tat.
• Is it near the train station that I depart from at 6am (!) the next day? Or will I need to wake up at ungodly hours to get to my train on time?
• Do the reviews say it "is more like a hotel" (ie: quiet, for the non-social traveler, and boring) or "has a great atmosphere" (ie: lively, people chat until the wee-hours, there's a requisite Australian backpacker dude in dreadlocks playing guitar somewhere, at some point)
• Why does this one hostel go by different names? My book lists it as one, HostelWorld lists another name, and google searches list yet another. But it's all one address, with the same pictures of the lobby/rooms. The answer to this doesn't help my search, but does make me feel a little less scammed. 
• Do I want the party hostel on my final night? Or the one with a free airport shuttle? It's difficult to say which is more important. 
• It's not the one with the sauna, and a sauna sounds like it'd be cool. Am I booking a hostel in a different city with a sauna? Never before did I want one, but presented with the option, this somehow seems important now. 

I'm booking that train ticket from Oslo to Stockholm! 

• Is the time of the ticket allowing me sufficient time in Oslo before and Stockholm after?
• Why does RailEurope list more train options than the actual train company? That's like Kayak showing more flight options than American Airlines' own website. If I book with RailEurope, will there actually be a train? Or is it imaginary?
• I'm booking this for the supposedly gorgeous views. Is it daylight in those wee hours at that time of year? (Checked that...it is) 

I'm booking that connecting flight from ___ city to ____ city!

• Wait, should I book the ferry/train/bus instead? Is there a ferry/train/bus? 
• Do budget airlines lock prices, or will these maybe go down or up in a few days?
• What are the luggage restrictions for this particular budget airline? Are there tons of fees for extra luggage, large luggage, a reserved seat, printing the ticket at home, in-flight snacks, speaking in English, or in-flight oxygen? Should I just book the non-budget option?

The stress...it piles on.