I will create several offline wallets from the virtual machine and send the bitcoins to them from the old wallet using my main machine as being some how paranoid here
I got that part. What I meant was asking if you are going to spend those coins often. Once you move your wallet from the offline machine to your main one, your wallet will be completely exposed. You can mitigate that by preparing transactions on the online machine, signing them on the offline one and moving the signed transaction to any online PC. This won't expose your private keys. Also, I don't think that using virtual machines is a good idea. If your host is compromised, so are your VMs. Using a separate computer would be safer.
This setup you are suggesting is actually and over-complicated Hardware wallet, after all. Where you store your private keys offline and use them to sign a transaction prepared on an online PC.
Regarding Wasabi, I am preparing a very Basic guide to run Coinjoins.
@scott.carter.2020 I will try to answer some of your answer on that one, and maybe post an international version. (even if I have the suspect the average reader I am referring to has way less technical competence than you.
A very good read on privacy, overall is this
A Treatise On Bitcoin And Privacy Part 1: A Match Made In The Whitepaper. I do recomment the read.