Sorry if this is a dumb question but how long do bitcoin receiving addresses last? Do they expire? Is there a time limit or a certain number of transactions you can receive to a particular address until it won't work anymore?
If you are using a wallet where you control the private keys like BRD, GreenAddress or Hodlwallet then you can reuse the same address as often as you like. If you are using a third party like Coinbase or Xapo to store your BTC then it's always better to ask them if you can reuse addresses.
I've never used any wallet, either custodial or a wallet where I controlled the keys, that did't allow me to reuse the same address. If you are using bitcoin for anything that is remotely illegal in your own country, then it's always best to use new addresses for each transaction.
if a particular wallet or exchange doesn't allow you to reuse addresses then i would suggest finding a new wallet or exchange to use. it's pretty standard at this stage.
While bitcoin addresses don't expire, it seems that Lightning Network invoices do. This may cause problems when crypto gambling sites start accepting Lightning deposits and withdrawals.