1. There are no customs issues because a new settler is allowed to bring in anything he likes without paying any duties. This is a one-time thing. I'm not sure how it would work if your goods are being shipped separately. My assumption is that you will land before the goods, so you will naturally have the BSF form and can email it to your shipper. I'm sure an experienced shipper will be able to answer this question, just contact a few and ask.
2. There are no tax implications for bringing money yourself. Again, you are allowed to bring in any amount the first time you land, even millions of dollars. You just need to declare any cash above 10k (cash you're carrying, not cash in a bank account). As far as transferring into a relative's account does, I don't know. Depending on the amount, he may or may not be asked questions when it comes time for his next tax return.