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Have you considered roping in someone to engineer/produce things? Might help keep your momentum/focus up if someone else can manage the DAW wrangling during the session and offer a bit of feedback between takes.
Otherwise sounds like you’re doing things right with the pre-production work and trying to get things right at source. One thing I would say is that most domestic environments are pretty terrible acoustically (especially once recorded) and that ‘natural’ sounding stuff on record isn’t necessarily produced ‘naturally’. Some close-micing in a dead room with subtle verbs applied afterwards can work very nicely and prevent that boxy sound.
Dramatic_Hammer
In terms of material, the stuff I have written falls into some kind of uncanny valley between folky pop and an approximation of sentimental singer-songwriter country pop of the 70s. I never claimed to be cool.
The acts I look to the most in terms of influencing songwriting would be the likes of Nick Lowe, Elvis Costello, Tom Waits, Neil Young as well as folkier stuff like Nic Jones, Nick Drake Martin Carthy and newer indie folkies like Joanna Newsom and the Decemberists.
It's musically simple stuff. Usually just picked or strummed on acoustic guitars and only a handful of chords. I want the focus of these songs to be on the vocal and the lyrics. I'm spending a fair bit of time in "pre-production" at the moment working and re-working lyrics though several drafts until i'm happy. I basically spend every spare minute of the day for a month or so with a notebook in front of me. I fall asleep with problematic lines going round and round and write endless lists of possible rhymes running through the alphabet in search of the right word.
Once I've got a lyric and a melody I'm happy with, I like to strike while the iron's hot and record it while it's still fresh. In terms of performance I find that multi-tracking what is essentially a solo performance loses more in feel than it gains in after-the-fact flexibility so I'm going for a live end-to end take of vocal and guitar in one pass on these tunes. I'm sure i'll come back to more complex arrangements soon but for now this live solo thing is where my head's at.
In terms of hopefully capturing a bit of spontaneity and spark I like to get a sound happening then just start running though takes till i'm fairly certain I've nailed at least one. I don't have a set method but the last couple of tunes I've done like this, I've sat down and knocked out 8 or 9 full takes then saved them and gone away for a few hours before coming back to listen. Somewhere around that amount seems to be the sweet spot for me at the moment. It seems to work in terms of still feeling the excitement of the new and being familiar enough with the material that I can play about with phrasing and maybe improvise a little bit . The main thing for me by doing this though, is that my voice gets warmed up and I learn how to sing it. By take 8 or 9 I sound totally different from the breathy choirboy with horrible plummy vowels of take 1. Hopefully after 45 minutes of consecutive takes, hot tea and maybe even a nip of whiskey the voice is working, warmed up and has a bit of character to it. Also (hopefully) by then my control of vibrato and pitch have woken up a bit too and the overall result should be a vocal that I can stand to listen to without wincing.
That's the plan anyway.