HKG vs MFM for departure to Taiwan?
 

Hello! I'm in the early planning stages of a trip to Hong Kong, Macau, and Taiwan. We will potentially add a 4th destination as well (Tokyo, Singapore, or Seoul depending on flight times and prices.) Based on time of year (end of April) and weather predictions, I'm hoping to go as "South to North" as possible to avoid going too far into the wet season, hence starting in HK.

At the moment, there are two potential flight itineraries I'm considering:

Option 1, all on a single itinerary through AA:
JFK - HKG (via LAX on AA 300 and AA 193. This seems fairly risky, there's a 52 min layover in LAX at midnight, but they are selling this as a single ticket...)

HKG - KHH on Cathay Dragon (after 5.5 days in HK/Macau. Would also consider losing .5-1 days in HK to get to Taiwan a bit earlier too.)

TSA - HND on JAL (after 6.5 days in Taiwan going from Kaohsiung up to Taipei.)

NRT - JFK on JAL (after 3 days in Tokyo. Have been before, this would just be a quick "for fun" stopover to eat at my favorite restaurants.)

Option 2, saves about $200 and removes the HK/Macau - Taiwan flight from the single itinerary:
JFK - HKG via LAX (same flight as above.)

MFM - KHH on Tigerair Taiwan, a bit earlier in the afternoon than the HKG - KHH flight on Cathay, but in this case we'd spend the night in Macau before instead of doing a HK - Macau roundtrip ferry day trip on the other itinerary.

TSA - HND (same flight as above.)

NRT - JFK (same flight as above.)

My initial thought was that saving $200 and being able to go into Hong Kong/out of Macau saves a bit of travel time. However, it seems there is more to do in Hong Kong so maybe we will feel as though an overnight in Macau is unnecessary and we can just see it in a day trip? Having everything on a single flight itinerary and avoiding a low cost carrier seems like a bonus as well, maybe worth the extra money. With all that said, I was wondering if anyone has experience with Hong Kong, Macau, and HKG vs MFM and can advise if one is more ideal for travel into/out of the area?

I wouldn't go to Macau for the soul purpose of flying out of MFM, but since your plans seem to include Macau anyway, I would fly out of MFM because the airport is super easy (no frills compared to HKIA, mind you).

It's a hassle unless you're planning to go to Macau anyway.

Small possibility of questions at check-in because you won't have a ticket out of HK, but you should be able to point to the Imm Dep rule that you don't need a ticket out if you're transitting to Macau.

Yes we were planning to go to Macau anyway, either as a day trip or overnight (unsure - does it demand an overnight visit?) If it's only worth a day trip then we may as well not bother switching hotels & lugging our bags and just fly out of HKG. We're not into casinos/gambling at all, just local food, market browsing, architecture, and general enjoyment of the area culture (a nighttime show may be worthwhile, that case, in lieu of gambling? Or even trying a nighttime bungy jump...)

Do you think we'll need proof in the way of ferry tickets to Macau when we leave for/land in Hong Kong, or would the separate flight ticket from Macau to Kaohsiung suffice?

An alternative we're considering has us starting in Singapore for 3 days on China Airlines (via Taipei), going to Hong Kong from there on Jetstar, then either doing the same MFM - KHH flight on Tigerair or Hong Kong - KHH on the China Airlines itinerary. I'm worried about using 2 low cost carriers, though, and am unsure of Jetstar or Tigerairs reputation (tripadvisor reviews look like any other airline to me.)

HK immigration will never ask for anything. It's always just a question of whether you'll draw a fussy check-in clerk who enjoys finding problems.

You'll lose a lot of time checking-out then checking-in again in Macau. I think just a day trip is fine for Macau, and on a short trip there's enough in HK to occupy you, so I wouldn't press you even to visit the place on this trip. Better to go there on your second visit to HK.