Hi @Diggingator. Welcome to the forum. Yes, there are a number of owners on THS with two homes. You might be able to swing it with one account, but it will require extensive editing of your listing (pics and description) when listing for the other house. It’s recommended to have two accounts, one for each house. Here is an earlier discussion:
https://forum.trustedhousesitters.com/t/listings-with-two-homes/