It is quite interesting how a simple question about recording a guitar generates so much strong opinions and becomes an “engineer” contest with people knowing “the only solution” etc.
I’ll give my 2 cents:
1/ Whatever style of music you do, you should be able to get a very good recorded tone from current commercial amp sims software (I don’t know much about the free ones, so can’t comment).
There are tons of highly successful commercial recordings in all genres (probably excluding classical) that are done this way, and it is now impossible (in a full mix) to tell the difference. (I mean, can someone seriously listen to a track on the radio and say “that was recorded with an amp sim” or “that was recorded with a real amp”?)
I suspect not.
2/ The common misconception about amp sims: People think they are meant to compare with the amp you are playing in the room. That’s not the case. They are meant to compare with the amp you have in the room being micked up and played back through your monitoring speakers (same as your amp sim). So, don’t compare “live” guitar sound with “recorded guitar sound”, it has nothing to do with it.
3/ yes, recording valve amps for real are great, and for some are the best way to get the tone they are after. But it’s far from true nowadays that it is the “only” way to get a good tone.
The suggestions I would make to the OP question in my opinion is:
a/ Put aside your Boss effect unit for now.
b/ use an amp sim and record direct into Sonar (guitar going straight into the instrument input of your sound card). Basically, eliminate any other source that can lead to confusion.
c/ Work on your amp sim interface to find a good tone, effects etc. You are very likely to find something you like with a little tweaking on the amp sim (as you would do with a normal amp)
d/ At that stage, only if you really feel the need, start bringingexternal pedals, your boss etc back in. But at least your core tone is good, and you will know if the effects are actually causing some confusion / really needed.
Of course, if you want / can afford, do buy top of the range amps etc. Of course they are great, of course they record well etc.
What I mean is: it is not compulsory you do that to get a GREAT recorded guitar sound. You should not feel like this is the only way.
You should get good tone with amp sims without having to break the bank.
That’s what I think anyway.
Good luck with it.