The answer to your question of why it’s so hard to give artists your money is exactly the same as it has been for ages for all media. The few companies who survived the consolidation of the industry have done everything in their power to make sure they are the gatekeepers of content. They buy and merge or kill off any competing companies or technologies.
They weren’t successful with MP3s or with streaming because they didn’t bother to understand the technology or that the Internet was the new marketplace and thought they could just do what they had done with physical media and pay for laws that protected their interests and sue everyone, but they ultimately lost control because you can’t sue hundreds of millions of people like you can sue a few thousand stores. So they had to give the people what they wanted for a while so they could have time to buy up all of the companies.
But they’ve now done that and paid enough to get the laws and precedents on interpreting those laws that they wanted, so courts are becoming better at enforcing those laws more quickly. So they can pressure new tech that pushes the limits on interpreting the laws to not last long enough to get people hooked. And now that they’ve reconsolidated most of the market and technologies as capitalism tends to do if you’re patient enough and there’s no possibility of monopoly regulation or market disruption, we’re stuck with pirate or use the garbage they feed to us and most artists are back to having to sign their art away and sleep with executives to get the marketing and distribution from the gatekeepers just to get a chance at success. The rest have to rely on word of mouth and self distribution which even online can be expensive without the advantages of centralized hosting providers, merchant accounts, and bandwidth.
Depends on how secure the application and the security you use in front of the application such as reverse proxies, load balancers, etc. If you are exposing a web application with no SSL, no two factor with, or something in a beta state or if you can’t trust your ISP not to create man-in-the-middle attacks for advertising and collecting information to sell which also likely introduces security vulnerabilities, then that could be a problem and a VPN or similar might be a big help.