Derek, if you find the work flow better in live, stick with live. If you can afford to cut your losses, I would recommend you go with what works for you. Samplitude is a great DAW, but if you find it counter-intuitive, it's not for you. I spent years in Cakewalk/Sonar and finally got Reason. Never looked back. The workflow was so much easier. I'm not saying Reason is the best DAW on the planet. But it is for me!
Foam will not help nearly as much as OC 703/705. Corner traps (you did not mention) will define the bass response in your room.
You have an AKAI keyboard, and an interface and microphone. It may seem like an awful lot of money, but I just put $8k into my studio this year...so a few questions:
What studio monitors will you be mixing with?
What headphones will you be using to track?
Did you hang a cloud?
What genre are you working with? This will define your workflow. EDM is different than Rap is different than R&B, etc. There are lots of things that will work the same, but you need to get your own flow and your own vibe going. And each song may be a totally different workflow. Keys first, beat first, guitar first, vocal first are all acceptable when tracking. I've done all of the above. Basic (and I mean basic) workflow for most. Write the song and get it recorded. Practice and re track everything that wasn't GREAT when you did it the first time. Trim and level. Mix it till it sounds absolutely fabulous. Add compression/limiting/effects (some of that has to be done during mixing to get the levels right). Send it for mastering (or do it yourself).
I'll give you the following advice on how to find the answers. No one can hand you the answers on how to use your studio, but we can point you toward them.
I recommend the free course from Berkely College at Coursera on Introduction To Music Production to anyone just starting out to get the basics in yer head. Get the terms down, get the basics of how to use effects/compressors/limiters/leveling amps/etc, some basics on signal path and gain staging, plus quite a bit more. This will get you going.
Read lots of stickys here. Go to each forum that interests you and read the sticky posts there...skim the big ones
TRY! If you don't experiment and get frustrated, you'll never have anything to overcome.
Ask pointed questions about specific things. "I set my limiting amp with these settings that were recommended and it still sounds like a cat being deep fried when I sing." and post a sample. NOT "What settings will work best when using a limiting amp?" Depends on the voice.
"How to I find the right frequencies to duck to kill my sibilance?" and "How do you use those frequencies to side chain a compressor?" will get you a lot further than "What's the best plug for removing sibilance?"
"How can I get better control of my pitchiness?" not "Please rate my voice."
Don't ask for opinion unless you want it. You WILL get both sides of any question if you ask opinion. "What's the best mike for vocals under $500?" will get you so many answers as to be confusing. You can find that answer by going to a local shop that allows returns and trying several in your own studio with your own voice. Record samples and post them and ask what sounds the best to trained ears...
Most of all. DO. Get into your DAW and figure out how to get it working the way you want it to.
USE the microphone and learn how it sounds best for your voice and style. Does it sound better when you have 3" between the mike and the screen or 6" or 9"? Does it sound sweeter if its head on or 15 degrees off axis? Do you sound better when you sing straight on or when you look up slightly?
Get that keyboard down. Know what every knob and slider and pad is for.
Happy Recording