Thank you for your insight and recommendations. Very much appreciated! 
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Since were mostly all ļ£æ nerds here, many of us look for integration with Apple Health (HealthKit).
For meditation, apps usually send data over to Health as āmindfulness minutesā. The Breathe app on Apple Watch is recorded in Health as mindfulness minutes. Calm and Headspace write to HealthKit this way. Not sure about the others mentioned.
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Another vote for Waking Up.
Iāve been using it for a year, time to renew. I will checkout Insight Timer. Iāve tried Headspace, Oak, 10% Happier but come back to Sam Harrisās app. Mostly personal preference of process and voice. I did start with Headspace and the FBH still uses it.
If cost is an issue, either by affordability or just not sure about the app, Sam does offer it for free if you email him, no questions asked! I think that is amazingly generous and you get a whole year to try it out.
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I had a bad experience with Calm, so I would not recommend it. I subscribed for a year and mostly liked it, but then I started having battery issues. I would use Calm for 5-10 minutes in the morning, then check my Battery settings later in the day and see that it had ābackground activityā happening all day ā 5 or 6 hours in some cases.
I reported this issue to them MULTIPLE times and only got a response suggesting that I force quit the app. I should not need to force quit apps. The background activity made me angry because it meant one of two things: 1) a major bug that they werenāt bothering to fix (unacceptable when Iām paying a hefty yearly subscription to support development of the app), or 2) some sort of nefarious background tracking of my activity on my phone. I realize #2 was unlikely, but it looked really bad to me.
Several incremental app updates came out during this time and this bug was NEVER fixed. You would think they would notice the bad optics of ābackground activityā and prioritize the bug, but they did not. I lost trust in them.
Then when I went to cancel it was a hassle. I had subscribed via their website (NOT the AppStore), and there was NO simple ācancelā or āunsubscribeā button. I had to email customer service and ask them to cancel my account. This was another black mark against them in my opinion ā donāt make it hard for me to cancel in the hopes that Iāll just keep paying you! This made me feel like the company operated in bad faith.
No idea if they ever fixed that bug, but I would stay away from Calm, personally.
They posted another āupdateā just to inform premium users that their subscription will be carried over to the new App, so I might be fine.
Most of the Apps suggested here look way better than Aware, but I got used to one of the voices in the App and I think Iām going to use their guided meditations to see whether I can make this a habit again.
I learned transcendental meditation in 1973 and have been meditate we since. I think to get the most out of meditation you should ālearnā from a teacher. Whether TM or another source. It is well worth the effort and cost.
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Waking Up gets my vote. I used it all last year. I enjoy the conversations Sam has with teachers and authors in the meditation field.
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insight timer hands down - love seeing my streaks add up its free for that component
and has alot of guided/paid classes if you want to go there
i agree w/ some of the comments I started on my own using headspace - and I did feel a difference but wow my mindfuless meditation practice took off to another level once I trained under a teacher. So many little mistakes I was making laying down - which some may do but my teacher focuses on mantra based, getting to those theta brain waves/subconcious mind programming without getting to state of sleep so the laying down doesnāt work for MY practice.
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youāre very welcome - good luck with it all
Sorry I forgot to mention, yes Insight Timer integrates with HealthKit
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Another vote for Insight Timer. I just use it for the timer and the tracking.
The same way you might pay a golf instructor to raise your game? 
Tried that, it didnāt work.
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If Calm worked well for you why not just renew it?
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Thatās what I did in the end. 
However, I wanted to learn about different options first.
Me either! 
Big headspace fan here. Am on a lifetime plan, so no yearly fees. My advice for choosing your meditation app: if you like the voice, try different moods. If the voice is able to center and focus you no matter what emotional state youāre in, then go with that. I just love Andy Puddicombeās voice to guide me along.
I highly recommend the book āThe Antidote: Happiness for People Who Canāt Stand Positive Thinkingā by Oliver Burkeman as a starting point for learning about meditation and general strategies for dealing with āhappinessā and contentment.
Iām a hardcore Insight Timer fan, mostly because itās free. In Buddhism thereās the concept of ādanaā or āgenerosity/charityā. The idea is that you should give as much support as you can, and Insight Timer is free for most of the content. I pay for their $60/year membership because I want to support them in their mission for providing such a good resource for free.
Iāve tried Headspace, 10% Happier, Calm, Meditation Studio, and more. I enjoyed them all. Overall I respect Insight Timer and its mission more than the others.
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Thanks for the mention of Oak. It was just what I needed and wanted. Perfect little app for timing a session.
Now I need to get back into the habitā¦
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Insight Timer especially for explorersā¦