Hi TuneMonger, I am afraid I am no professional singer and I barely qualify as a musician, but I am going to give you my opinion anyway.
First of all, I think you are selling your voice short. I haven't listened to every song, but I sampled a few.
In "Loveland" your voice is not bad at all. It kinds of reminds me of "Chet Baker Sings" as far as style and phrasing. I think that with a bit more practice you could do a good job with that one.
Speaking from experience, those of us that think we cannot sing tend to make things worse by giving up before we even start, but in this song, at least in the first few bars, you do OK. Better than OK, in fact.
In some of the other songs, you are a bit out of tune, but that's what practice and singing along with a piano (or Melodyne) is for. To me it's cheating only if you are a professional singer and get plenty of plays in Spotify, while overusing Melodyne. Otherwise for us amateurs, a little correction here and there is not a mortal sin.
More worrisome is that hesitancy you display in some of your phrasing. That's because you are unsure of yourself and, at least in one song, something went wrong with your microphone/mixing. The result is a kind of distortion that may work well for a guitar, but not for voice.
The hesitancy is probably also due to lack of practice. You sound tentative. But I could be wrong. Maybe this is the result of months worth of practice and I am full of it. Still, I don't think so.
My suggestion would be to keep practicing your strongest songs until the sound of them makes you puke. Wait a week or so, and try again. Only this time approach the recording boot with more self assurance.
Look, I have the same problem. Mine is compounded by the fact that I have a noticeable Italian accent. Some songs or genres (like blues) are completely off-limit for me.
Yet I persist because I play music for fun, I can sing in tune most of the time and it makes me feel better. Plus, I have to have something filling the gaps in between guitar solos
Allow me to share a story with you.
I sing while either playing the piano or guitar and I have a Mixer/PA that I use for that touch of reverb. My wife, whom is nobody's fool, lets me know precisely what I do wrong and what I do right.
According to her, both my playing and my singing are getting better, but my accent is the kiss of death for some songs and I lack practice and confidence.
However, the other day I arranged and sung an old Italian song that used to be my warhorse in high school. Nothing anybody in this forum would recognize, but a pretty famous song in Italy in the 70s.
My wife actually got out of bed (That alone should have been breaking news on CNN) and entered my music room unnoticed. When the song was over, she told me that she thought someone else was singing and that it was the best singing performance I had ever done with her around.
That made us both think.
The conclusion we reached is that my unexpectedly stellar performance was due to a few factors:
1) My voice was warmed up (Red Wine works for me)
2) Despite using a MIDI backing track and my guitar, the arrangement was passable
3) I knew the lyrics by heart, rather than read them on screen while also trying to find the right chords on piano (guitar is easier for me)
4) Most importantly, I sung with confidence, something I find hard to do when I sing in English.
Since then, I have been trying to find that same confidence in other songs, with mixed success, but at least I am trying. Practice helps a lot. I practice singing the melody in unison with my piano or guitar and I actually read the melody's notation.
What also helps a lot is to memorize the phrasing and lay down multiple singing tracks. A bit of slicing and dicing and you can pick your best vocal performance out of several takes. I am sure you know that, but I want to make sure you know there is no shame in that at all. Most of the songs we grew up with, save for live performances, were recorded that way.
I believe we share the same problem, but I also believe that you can totally sing your own songs. Focus on your best ones first. Sing them until you want to vomit each time you hear it, and I am sure you'll get better.
Getting back to Chet Baker, he was not a powerful singer, but he sung with such intimacy and passion that some of the standards in his album "Chet Baker Sings" are among my absolute favorite interpretations.
Good luck.
When that is all said and done the final magic is the mix, for pitch, EQ and FX. I am not being critical, but are you doing everything you can in the mixing stage to get the best you got to give?