Two trips away very close together

That might be ideal for you, but finding a sitter for whom a schedule like that will fit into travel is unlikely – not impossible, but unlikely. Unless you have a super big home or a separate guest house that you airbnb, and could host someone in your home as your non-sitting guest for five days, allowing both of you a fair amount of privacy, I don’t know how you would manage it.

Here’s a cautionary tale of someone who hosted a sitter who wasn’t sitting: BEWARE of Sitters that just want a free place to stay - #67 by Rlean808

The other issue with this is it kind of locks you in to a sitter. What if you came home and found things weren’t great? Would you go on with the second sit?

If you post both dates, you might find there are some sitters who are open to doing both dates, and you could prioritize those applicants. You might find no one would be interested in the gap.