Decision made. ENVOY. Here is how I thought through things after taking in all the comments here and doing a lot of soul searching.
1) Envoy will be a serious challenge since I have not flown in over 6 years (other than the Flight Review and IPC I am doing this current week). I will try to afford to fly some more beyond this if possible before I start since I have access to a DA40 I can get checked out in. But depends on me winding down other responsibilities as well to get to Envoy with zero commitments outside of excelling at INDOC, SIM, and IOE.
2) Recruiters kept saying due to my appoximate 2000 hours of prior 121 time about a decade ago as an FO and my 5000 hours total time, I'd be a DEC. I'm hoping they can do something like make me an FO for the first 250 hours then upgrade, but if not, I will come mentally prepared for what ever challenge I am presented with.
3) Envoy will be difficult for the first 5 years until I can get to a Miami base (I figure it's about 5 years from what I hear, but i'll plan for the worst and hope for the best). If not MIA, my goal will be to enjoy PHX until I get to MIA (and what ever else may happen before PHX). I'll rent an apartment in base and commute home only when 4 or more days off in a row. I also have family in PHX too. If I only get home to Tampa Bay once a month, that's okay. Once they get PBS going life will be good even on reserve if they allow what Mesa allowed using PBS (6 on, 2 off, 6 on, 2 off, 6 on, 8 off).
4) Once at MIA in the distant future, life will be great. It's not a bad commute from TPA to MIA. Plus South Florida is a place I may consider moving to once based there since I love the beach lifestyle. And while I prefer the Florida Gulf beaches near Tampa, I'm sure I can find the right beach in South Florida for me. I'm thinking long term. After all, this is a career where sometimes we have to "pay our dues" to get to where we want to be. And Envoy has always been the place I wanted to be, I just was never offered the opportunity before now.
5) If I turn down Envoy, I will never be able to consider them again. It's now or never due to how seniority works and the mandatory 65 years old retirement age. I'm not 35 anymore, so I need to consider very carefully my choices. Flexjet and similar companies where there is no age limit will always be there for me should I chose to keep flying after 65.
6) I love the 121 world and I at least am familiar with it. I love knowing in advance where I am flying and when. Sure, for the first 5-6 years I'm on reserve so things just will pop up. But the route structure will become known and comfortable. And I really like that over a Flexjet where every day for life it will feel like being on reserve as trips pop up to random places. Very odd for someone who is loves the unknown in all other aspects of life. But with my flying career, I prefer the known.
7) I love flying the E175. Have some hours in it. Really loved it. My favorite bird I ever flown.
8) I have several investment properties to maintain in the Tampa area. Harder to manage from afar and then I can not be there. But, it can be done. I am implementing plans now to still be able to be hands on from afar by having a good system in place where I can accomplish almost everything remotely using various connections and resources. And worst case, if my idea does not work. I'll sell and invest elsewhere.
9) Flexjet will be much easier lifestyle since I'd be home based and get 12 to 14 days off every month. But this is literally the only positive I can think about. And while it's my most important bullet point, all other bullet points tell me to go to Envoy. Plus, if I do not go to Envoy, I'll always wonder if I made the right decision since I always wanted to work at Envoy. Even if things were going well at the place I chose that would not be Envoy.
I actually look forward to PHX and then MIA in my future. And if it takes ORD and DFW to get to those, that's okay as well. I'm ready for it. Would love if Envoy let's me come in as an FO for 250 hours and then move to Captain, but if not, I'm also ready for that as well. So Envoy it is. I'll sign the CJO after I complete my Flight Review and IPC. Plus I need to be back home to gather all the info requested in the CJO since my flying this week is 500 miles from home. I chose to go with an instructor I had in 2008 that has a nice TAA and is outstanding (prior 121 pilot as well) versus some fresh chap right out of flight school that is just building hours.
Thank you everyone for all the input. And sorry for the novel. But you can see, I thought it through extensively over the last week.
