Hi all, I was wondering if you wouldn't mind helping a board lurker out with some questions I've got... I'm planning way ahead for a 4 day weekend, and it's my first time making travel plans for myself.

Where to begin... okay- so, when I'm purchasing the tickets- what would be the least hassle- find a cheap price online via a travel $ aggregator, and then make individual plans with the airlines, or should I find a good agent to help me?

Airport- I'm planning on at least an extra hour to get past TSA and arrive at the gate early... any variables there to look out for? Already seen that TSA horror story where the person was forced to fly soiled in their own urine or something...

Upon boarding... I use a manual ultralightweight chair, so I know to take my seat/ back with me, and we can disassemble it and put it in an onboard closet... and can I request not using that aisle chair and trying first to pop right into the first row? -Course that's dependent on if it's assigned seating, right... does anyone have any input on which airlines are easiest to work with / a pain? [Chicago to Seattle- Alaska Air seems to be whom i may use]

Gosh, I had a ton more questions, I'm sure of it... would everyone mind helping me fill in the blanks and give me a better idea what to expect? Had a hotel question or tow also, but can't even remember them atm... thanks for the help!