I have been reading thread after thread from several Regionals and believe Envoy may be my best bet based on circumstances (Yes, I will look at Endeavor, but hear me out).

First, you have to know the situation:
Most restricting is age - I’m 52. Currently in Part 135 Scheduled Operation (I know there is back and forth debate on that for upgrade). I will be out of my contract in about 13 months. Will have over 2500 TT and 1300 ME. No turbine. Clean record.

Coming from the medical business which is very unstable now, I know I got started in this business late, but always loved aviation and betting on the pilot shortages to boost this opportunity. Obviously the biggest thing I face is age and mandatory retirement at 65.

Since my biggest priority is retirement and you need 10 years, I only see two paths:
1. Go END and retire there for better pay/benefits and never leave
2. Go Envoy flow to AA and retire with AA. Not 100% sure, but I think Envoy, PSA, and Piedmont are the ONLY regionals that credit time served there toward the main liner (AA). Does anyone know for sure? This is the ONLY path I can see to the Majors and get 10 years in. I would have a total of 12 years in the “AA system” - however long it takes to flow

Envoy Pro/Con
Pro - possible retirement with AA - HUGE (I believe they are Number 1 in travel benefits and that’s a high priority for me to travel around the world)
Pro - Getting based in MIA (I don’t see much talk on this base as the other three). I know the seniority goes LGA, ORD, MIA, DFW.
Cons - Moral and Pay/Benefits

Questions:
- Can we stipulate ORD (2nd junior base at hiring)?
- When should I start applying - 6 months before contract ends because of slow class dates?
- How long to get to MIA?
- Obviouly the BIGGEST question is the path to retirement- Stay Regional or go Envoy with flow to AA, ONLY IF its true time credited.
- What are Regional retirements like? I know that’s an uncommon question because they are used as a stepping stone - not a destination

You start at year one again with AA. Time served with Envoy counts towards your total time calculation required for lifetime travel benefits.

So in theory, 9 years at Envoy and 3 years with AA= no retirement and flight benefits?

Strictly speaking about being able to get retirement travel- your time at Envoy and AA will count together. That being said, the retirement travel is exactly the same at AA as it would be if you retired at Envoy. What other retirement perks are you hoping to gain by retireing at AA over Envoy?

No your longevity is carried across to AA for the purpose of lifetime travel benefits. You can also roll your Envoy 401k into you AA 401K.

I’m not sure what else you can carry over to AA, your seniority at AA certainly starts back at year one.

As much as I have been researching this, I have not fully looked into different retirement perks because my options are very limited.

To be clear - 12 years in the “AA system” would get me what?
Is AA flight benefits better that DAL?
Would the retirement perks say at END for the full 12 years (No time counted for DAL - so hiring with Major probably not a good idea) stack up against 12 years Envoy/AA?

Yes, then there is the whole QOL/Pay thing along the way.

Anyway to put ORD in your contract?
How long to get to MIA?

I get seniority starts over. May not want to flow if its only for a year or two, to be at the bottom again.

A lot can change in just 5 minutes in this industry so what is on offer right now will look vastly different by the time you flow.

Yes, you will start over at the bottom of the APA seniority list, but you will carry-over the Envoy time towards travel retirement benefits. Trust me, I've already looked into it.

In your case, the better option is to upgrade quickly and get the PIC time.
Once you have 600-1000 PIC, put out apps to Delta, United, FedEx, and UPS to name a few. The coveted AA flow is crap to get Envoy stacked heavily for the future, but can it be jumped with the right connections.
That is what I was considering, but I believe there are better options out there, at least in my case.

Good luck in deciding whichever route to go...

By the time you reach flow, you will probably have enough seniority that you don't want to flow for what little you would gain at AA with the short stint there. I would pick your airline based on staying there for the duration and have apps out for the majors and hope you get scooped up before you get too for down the line.