Hi Dave!
Firstly, I don't know the answer to your question! (sorry)
This is a question that I struggled with more so in the past than in the present (so less so in the present than in the past ;) )
From my own experience, I haven't been on any retreats and have been practicing for 5 months 1/2 hr in the morning 1/2 hr in the day. I mostly practice mindfulness of breathing, walking and bringing mindfulness to as many tasks as it occurs to me. And I practice with a group with the (facilitated) teachings of Thich Nhat Hanh (that has 3 teachers (facilitators, the idea being that one kind of acts as a conduit/embodiment/stream through which the teachings of Buddha flow). I am engaged to be married in the summer, have an apartment, a cat, a dog, an aquarium (with fish) and a crazy family

(I think crazy is redundant haha).
Where am I now?
A bit less self absorbed// more aware of others
A bit less anxious (sometimes more so sometimes less so)
A lot more aware of this moment (compared to when I began)
I've had experiences of expanded awareness, a totality of stillness, serenity, joy. I've also had experiences of dullness, fatigue, fear, doubt... wait lets say DOUBT!

All of those experiences are temporary... (I imagine any experience of enlightenment would be the same)
So objectively, I'm not sure that is progress and I haven't had any, "holy s**t I'm part of everything and stuff" experiences yet. But I'm not as worried about trying to get those either, so for me I would say that is progress. I'm more concerned about making sure I do 1 hour total each day. I am going to try and go on retreats, but at least initially I can't imagine being able to go on one longer than 1 week.
I seem to have the same intentions as you (as you outlined). I want the big E, Buddhahood, cessation of suffering, nirvana etc. I've found that very same desire has in turn caused me much suffering (in a good way!

) The facilitator in my group told me little things lead to big things, so maybe the best thing to do is just to focus on the first step

She also said the future is made of the present, so why are you worrying about the future? Oh and also! Be compassionate to yourself!

(that one I've found is very important!!!

)
By the way, Brad Warner (head of the Dogen Sangha group... you can look him up), explicitly states that all you have to do is 1 hour of zazen (which is basically just sitting) each day, and just focus on that. I'm pretty sure he's the real deal (and he's at least cultivated the image of a regular dude... I can't say for sure as I haven't met him) from the books I've read. I personally, found zazen hard at the beginning... although maybe if I tried it now it would be different.
But I still gave anxiety about attaining enlightenment! Had a bit today

and I'll probably have some tomorrow!
If you can practice with a group of people (with a few who have a decent amount of experience) and you like the vibes then I would suggest to do that. I think it's much harder (probably) to just go out on a limb by yourself.
So start practicing! Don't worry about the future! Focus on the now! Be Joyful! Be Light!
(hopefully I wasn't unhelpful)
May your practice be fruitful, may lotus blossom beneath your steps, may each breath bring you happiness and joy