Confused, should I go segwit for seemingly lower fees?
It is good to go for segwit than wasting more btc on transaction fee, you can reduce money on fee significantly if you use segwit. There is a topic in beginners and help that can help you know more about the fee paid which is low in segwit. Why do you need both segwit and legacy addresses? Before you make your decision, you will pay more fee why using legacy address for payment.
Legacy have the high transaction fee
Nested segwit (3-prefix addresses) can reduce the fee up to 26%
Native segwit (bc1- prefix addresses) can reduce the fee up to 42%
Also know that you can transfer bitcoin to any of the addresses, you can transfer from segwit to legacy or from legacy to segwit. But using segwit will safe you fee while making Bitcoin transactions. The reason best for you to just send your bitcoin to native segwit addresses.
Legacy have the high transaction fee
Nested segwit (3-prefix addresses) can reduce the fee up to 26%
Native segwit (bc1- prefix addresses) can reduce the fee up to 42%
Also know that you can transfer bitcoin to any of the addresses, you can transfer from segwit to legacy or from legacy to segwit. But using segwit will safe you fee while making Bitcoin transactions. The reason best for you to just send your bitcoin to native segwit addresses.
Just a small correction:
Using native segwit addresses, the transaction fee can be decreased even by more than 42%.
The transaction fee is decreased by 26% when there are 1 P2SH input and 2 outputs.
The transaction fee is decreased by 42% when there are 1 bech32 input and 1 output.
For example, size of a transaction including 10 bech32 inputs and 1 output would be about 722 vbytes and 1524 bytes. That's more than 52% reduce in transaction fee.
Using native segwit addresses, the transaction fee can be decreased even by more than 42%.
The transaction fee is decreased by 26% when there are 1 P2SH input and 2 outputs.
The transaction fee is decreased by 42% when there are 1 bech32 input and 1 output.
For example, size of a transaction including 10 bech32 inputs and 1 output would be about 722 vbytes and 1524 bytes. That's more than 52% reduce in transaction fee.
The best you can reach is around a 54% reduction. A P2PKH input is 148 vbytes, while a P2WPKH input is 68 vbytes, for a difference of 80 vbytes. 80/148 = 0.54. There are of course other differences between the size of outputs and the size of the transaction header, but these are very small compared to the size of inputs.
You shouldn't move your coins now to a Segwit address. There is no need. You are going to pay fees now, to pay less fees in the future? It is not worth, imo.
It depends on the amount, he can decide to transfer 0.01 btc and make more than 10 transactions from it. 
