To the OP,
I wish you lived here near the Beach. I would welcome the opportunity to work with you. It appears that you have been around the block a few time also but find these new fangled methods a bit daunting. You probably already know all of this but;
The skilled recording engineer is part perfected craft, part art that is developed after many years and 1000's of studio hours of trial and error, experimentation and learning what works and what doesn't. Regardless of what people say today, you are right that the console and tape imparts it's own special character into the recording. That's part of the reasons why different studios had different sounds and they were chosen by the producers for their
sound and sometimes the musicians they had waiting by the phone for work. It is also why developers today spend hundreds of hours modeling those analog circuits trying to create in the digital realm what made gold in the analog and hoping they can capitalize on those sounds. They a getting closer a little bit at the time, year by year.
As an aside, it's also true that part of that sound came from the room, but as the recording art form developed, engineers did every thing they could to eliminate the room sound through close micing. Some room character was still added and in some cases utilized, as in the famous case of the exact position the mic was placed for Karen Carpenter at A&M beside the control room window to catch those reflections, but mostly the room sound was undesirable and engineers relied of the console, tape bump and outboard hardware to get the sound.
That console is really the big part of the magic. It was and still is almost organic. All that iron in the transformers in the input and sometimes output stages. The magic imparted by a particular console was part of what made a studio choose a particular board. It gave what BECAME the trademark sound of that place.
The tape recorder also imparted it's sound. There where more hits recorded on a MCI JH24 than probably anything else. It was and still is a huge sound with, in my mind, a glassy shimmer in the high end that's still unobtainable in the digital realm no matter the bit depth, sample rate or how much you pay for convertors. Certainly it was used at Muscle Shoals, Memphis American Sound Studios, and Criteria among others. Hit after hit came off those machines. It was the radio sound we are still trying to achieve.
The characteristic openness of and sizzle on top of a vocal recorded with a U47 or 87 is unmistakable but mostly never even noticed by the average listener. They just know it's great. But it is a large part of what made any recording a great recording. Conversely, a RCA 44bx will make any voice sound absolutely huge, in your face right there, with no shrillness at all and fantastically open and it's perfect for a song that calls for that sound - and especially for a nasally voice.
There is to this day nothing that I am aware of that can put a vocal just on top and keep it on top like a Universal Audio LA-2a leveling amplifier. It is magic when it does what it does. And a Manley Varimu will glue a mix together it a way that cannot be described - it just does what it does perfectly.
Problem is, all that stuff, just as John said, was and still is, very expensive. I am nobody at all for sure but having spent most of a adult life in recording studios (I am old) and carefully studying, analyzing and listening while doing my music thing, I have seen both sides. Analog is amazing. Digital is amazing and it is getting better all the time. Except for my home, I have also spent most nearly every dollar I have ever earned trying to capture that elusive sound. It sure is a hard road to hoe, to use a old saying.
If I were really looking for the character that is added by that well chosen gear in analog the realm while remaining in the digital, I would start by investing in UA plugs. Those folks really care about modeling and they have a unmatched heritage to live up to. I have nearly all their stuff and it is astounding how good it really is. But even with those, I still keep a real UA-LA-2a on a vocal track, a real Symetrix 525 on the stereo drum channels and the list goes on. There are just some thing that hardware does better.
For quite sometime I used a Tascam digital mixer with Sonar. I adored the audiophile quality I was obtaining although it had that characteristically annoying (to me in a minor sense) high end shrillness, but it lacked character. None. What you put in, you got out. So when Malcom Toft announced around 6 or 7 years back that he was going to build a smaller/less expensive version of the Trident console, I leapt at the opportunity to own one. I can't even begin to think of the astounding records that were made on Tridents. I'll probably never have a hit, but at least I have the sonic character of a hit. Sonar is more than capable of doing it's part too. My 16 track machine sits idle over it's corner, day after day, synchronizer on, timecode running and all ready to go. But with the sound coming from my personal selection of assets in the studio and out of Sonar, I see no point.
I don't know how long it will be before the younger guys will be able to really emulate the sonic character imparted by analog gear, on the records my generation grew up with and loved. I don't know if they will even want it or appreciate it when they hear it. I suspect most average listeners won't. And that is sad. But I do know that today, just like days of old, to purchase and own the hardware stuff is expensive. I feel blessed beyond belief to have such fabulous tools available. I cannot comprehend why young folks are not standing in line to intern and learn the process. But there is no interest.
DAW's have at last made it possible for someone to set in their bedroom and attempt to emulate what just a few years back required dozens of folks to do. Highly skilled people. From Composers, A&R directors, copyist, arrangers, producers, studio engineers, a select few tested studio musicians that knew what would work on the radio such as the Swampers, Wrecking Crew, American studio band in Memphis, or the Funk Brother, Memphis Horns, backup singing groups galore, Mix engineers, Mastering engineers, and the list goes on and on.
Music recording was an entire industry with thousands of people adding there particular talents to the process. And it was damn expensive.
Basically, you can get close to analog if you really dig into Sonar. I know that Cakewalk touts the modern hits made with it so I am sure it is possible today to make music with it that will be accepted and with the "modern" sound. But regardless, it is a steep learning curve. Greg Henderschott, the originator of Cakewalk recognized early on that as the software became more and more complex that it was going be able to do a lot of things some people had no interest in and add increased difficulty in understanding it. He was a very forward thinking person and I miss him.
But if you hang in there, you will be pleasantly surprised at how quickly you will pick up tid bits here and there, a sense of comfort will be reached with the software and after a period of time, it will start to come together.
Good luck and keep up posted.