"First Class" Questions....

Given that they’re now barring flights 40-45 min prior to departure, I would absolutely not risk a less than 60”connecting flight. You may board your first flight on time but there could be unseen delays that cause you to miss your. You might also risk your checked luggage missing such a tight connection.

Agree with others that 1st class isn’t worth it in shorter flights. Why not sit in economy plus right behind first?
Just because they are boarding 40 minutes before scheduled pushback doesn't mean you have to be there 40 minutes before pushback. You only have to be there 10 minutes before scheduled departure time. If my options are a 35 minute connection or a 5 hour connection, I'm going to try. Obviously it works often enough for the airline to sell it. I've had multiple flights where my bags made the connection and I didn't due to a late inbound.
 
Sometimes you get the Pre-Departure Beverage. I did not get one MCO-DTW on Monday, I did on the way down, but not on the way home.
Oh the PBD debacle. I always get a kick out of the threads on FlyerTalk dedicated to did you get PBD on your flight?
 
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…it will be just me and since I can check 2 bags, I will probably only be carrying my purse so I won't be hauling any luggage…
Don’t do this unless it’s a massive purse. You should always fly with a full change of clothes and any items you deem absolutely necessary to your trip. Airlines lose bags ALL the time. Yes you can AirTag it to know it got left behind in Chicago but you’re still gonna need a set of clothes to wear to the park while waiting on your bag to get to Orlando. Bring a small carry on.

As far as pricing, if your dates are set and you can afford it and you find a flight you like book it. Because what are you gonna do if the price goes up? FC flights swing just like economy/e+ With the anxiety I disagree with others as far as downgrading to e+ and recommend sticking with FC if you go the connecting route. Every FC has noticeably more room than e+. As FC you will be off the plane really fast so I would not worry about any connections >50 mins even as a slow walker (35 is too tight for the slow walkers in my crew).

I would be sorely tempted to ditch FC and take the direct but I haven’t dealt with your type of anxiety. Have a drink or two in the airport, a totally distracting movie ready to go on your tablet and get it all done in one flight.
 
Perhaps with all the negative variables you are encountering trying to do it "by myself", take your friend's advice and see how that looks.
 

I fly first class pretty much 100% of the time. But in the OPs case I'd look at the nonstop on Frontier and their Business bundle. They now have several rows in the front that have extra leg room and a blocked middle seat. I think if the front row is aisle is available that would offer a similar amount of space and openness as a legacy carrier's 1st class. I priced out a random Saturday in Feb and it was $325 and included bags and seats and priority boarding. Up Front Plus is what I think the option is called.

https://www.flyfrontier.com/travel/travel-info/seating-options/?mobile=true
 
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Thank you all for the great advice!

It looks like we may have a solution! We found a flight on AA that flies out of GRR and connects in PHL. Coincidentally, my friend was planning to fly out of Allentown and the flight she was looking at connects in PHL to the same one! I will have to deal with a CRJ from GRR to PHL which will be awful, but I will be sure to medicate myself and I will have the assurance that I will be able to meet up with her for the remainder of the itinerary. This is a much better option. I don't think I have ever flown on American so hopefully it will be a good experience. They are really going through it lately and I feel so awful for them. I've been thinking about those employees a lot lately and cannot imagine how hard it must be for them to go to work every day.
 
...and now ALL of this is moot! SWA released their schedule and I have a NON-STOP option out of GRR that is cheaper than every other airline! I could not believe it! On top of that, my friend found a non-stop out of PHL that lands within 10 minutes of my flight! The stars have aligned. With a non-stop flight, I can deal with my anxiety by taking my xanax and enjoying a beverage or two, knowing that I have a full 2.5 hours to relax and chill out with a movie and my headphones.
 
For me, I just have to scroll further down to see them. I don't like that AA doesn't allow you to filter by connecting airports. My local airport has one flight a day to CLT, I can see connections of 55 minutes, 2 hours or 3 hours.

It is, infinitely more doable than 35 minutes at ORD. And I've done and made both. RJs will come in out at C, then you will have to walk through the tunnel to A, where in A your MCO flight leaves from is going to be the unknown. But I was shocked at how small the DTW airport actually is. Ground transit time there is nothing like it is at ATL. ORD, CLT or even MSP.
My recent flights GRR to MCO on Delta through DTW have put us at the furthest gates in A from C. Even using the tram, it’s still a hike. If the flight from GRR is at all late, connection will be missed. I had a 55 minute connection time last trip, we were 15 mins late. I did make the connection, but they started boarding right after I got there.
 
My recent flights GRR to MCO on Delta through DTW have put us at the furthest gates in A from C. Even using the tram, it’s still a hike. If the flight from GRR is at all late, connection will be missed. I had a 55 minute connection time last trip, we were 15 mins late. I did make the connection, but they started boarding right after I got there.
If they started boarding just after you got there, you had at least another 25 minutes before you would have actually missed the flight. The requirement is that you are at the boarding gate at least 15 minutes prior to listed departure time. Delta begins boarding 40 minutes prior to stated departure time.
 












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