I've been Home producing for around 20 years now, but I've had the below setup for at least the last 5. After all the experimentation and expense with trying different setups, this one just works, and allows me to focus on the creative side of making music.

PC - Although I've quite a modest PC, I've added as much RAM as I can (16GB). RAM is fairly cheap, and is the most important affector of DAW performance.
DAW - Ableton Live 7. Simple, Intuitive, clean, and comes with a great range of instruments. I've resisted the urge to upgrade to 8 or 9 so far, but would highly recommend it.
Drums - EZDrummer 2 - Great Sounds, Great arrangement/song structuring tools (Starts, Verses, Fillls, Choruses, Middles, Endings) Easy implementation in Ableton.
Pitch Correction - Antares AutoTune of course!
Mastering - iZotope Ozone (5 I think). Just select one of the many presets, drag it onto the master track, instant polish.
USB Interface - BOSS BR-800 - Inbuilt COSM guitar and Vocal FX, which means zero latency.
Edirol Monitor Speakers
Shure SM58
A decent set of Headphones.

All Guitars / Bass and Vocals get recorded direct (zero latency) with any additional effects being added through Ableton. This way I can put the maximum effort into recording without being but off by a dull dry monitor mix.

What's your setup?
Ableton is awful DAW for anything but dj beat slicing. They didn't support meter changes from what I remember, so you start 4/4, you had to end with it. Anyway, if it works for you, and is intuitive, that's all that matters.

I'm on Studio One now, firewire FP10 into 3 year old HP laptop or desktop that is custom build). Alesis Monitor One Mk2. I also have a travel interface, Edirol UA-4fx that is kinda like your Boss, it can do a few tricks like guitar processing, tube emulation, some compression, even loop recording with mastering options. I don't use these much as it is better in the DAW, but sometimes the tube emulation and compression help bass and vocals to sit in better in the track so I use that.
I also have Izotope mastering plugins via Sonic Foundry or use S1 Producer's mastering options which are quite robust.
Drums - more and more Ezdrummer, even though I still use my Boss Dr. Rhytm 880 occasionally.
I've been at it about 15 years. My home studio setup is here: www.greenroomrecording.ca

Could I get some more talent in the monitors, please?

I know it sounds crazy, but try to learn to inhale your voice. www.thebelcantotechnique.com

Chris is the king of relating music things to other objects in real life.
I still use a hybrid system . I do my tracking on either my older Tascam 2488 or my new Tascam DP24. Both are 24 track digital recorders. In my computer I use Sonor or Cakewalk Music Creator to mix and edit my imported tracks (USB download with the 2488 and transfer from an SD card with the DP24). I like to work fast when I am doing the first tracking (record in haste, edit at leisure) so I like being able to just hit my footswitch and record. I like the Tascam routing system that allows you to move the input to another channel just by hitting two buttons so you can overdub guitars or vocals quickly by just hitting a button and moving to another channel.

For mastering I use T-Racks Deluxe Mastering Suite. I love this group of VST's. You can either use the pre-programmed mastering choices or create and save your own setting. The T-Racks emulations of classic gear like Putec are excellent.

As far as hardware I use a Tascam interface to send my mixes to either my older JBL Studio Series monitors or my Behringer Truth monitors. My computer is a system designed by my son and I am currently upgrading it to a new system that he is building for me with better video cards and graphics capabilities more ram so I can do better video editing.
Yes I am guitarded also, nice to meet you.