I think there's nothing wrong with offering a bounty for certain kinds of issues. Caveats:
1) it would need to be the kind of issue where it's pretty clear whether they did an acceptable job or not; some kinds of rearchitecting would just not be objective enough
2) you cannot assume that it will work; it should be a "nice to have" kind of issue, not a "we need this for the roadmap why hasn't someone done it yet" kind of issue
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I think there's nothing wrong with offering a bounty for certain kinds of issues. Caveats:
1) it would need to be the kind of issue where it's pretty clear whether they did an acceptable job or not; some kinds of rearchitecting would just not be objective enough
2) you cannot assume that it will work; it should be a "nice to have" kind of issue, not a "we need this for the roadmap why hasn't someone done it yet" kind of issue
3) there is a lot of discussion among psychologists about the consequences of putting money on something, you might want to read this and ponder it: https://priceonomics.com/effectiveness-of-fines-for-late-pic...
Having said all that, I don't think anything horrible would happen if you just tried it out to see if it worked.
Spot on. Most bounties are tiny and, as a FOSS developer myself, look discouraging or even a little bit insulting.