To my understanding, I can generate 3 (4??) different addresses from my private key:

* Legacy address  1ABCDE..... (plus one in uncompressed format)
* Segwit P2SH address   3ABCDE....
* Segwit Bech32 address  bc1ABCDE....
* P2SH multisig address (1-out-of-1)   3ABCDE.... - unsure

I can send coins to all of those addresses, and to 3rd party observer that will look like balances on different unrelated addresses.
If I'm correct, are there any flaws or security risks in this?
And if I'm importing private key to some kind of wallet software, how wallet determines which address to scan on blockchain and which balance to consider as wallet's balance?

Thank you for your answers, I realize there are chances this is a pretty dumb question :-)