Hi @jakemiller firstly your approach is the right one, apply for local sits and more than one at a time and when you hear back from one in a positive way and confirm the sit if necessary advise other owners that you are no longer available.
Perhaps in your applications be clear about who will care for Louie while you are sitting as you are obviously a loving and connected team and owners may assume that you will want to bring Louie along too. … some may even invite him (he is adorable) if he gets along with other dogs and they have the space.
Your profile is great, pics are really good (well you are a photographer:)) and you have great references. When applying for sits make an effort to craft a personalised application which shows you have really read their listings, I’m sure you are offering to meet first and of course, if you can be flexible, apply for last minute sits, with all of the uncertainty around today many are leaving plans until the last minute.
Some newbies get a sit with their first application, others take longer it took me two months and numerous applications but once I had that first one I never looked back.
Also set up a saved search for Chicago so that you get notifications of sits and can apply straight away … https://support.trustedhousesitters.com/hc/en-gb/articles/360002090298-How-do-I-create-delete-saved-search-alerts-on-the-app-
Also there are great conversations on the forum around getting started and first sit applications, using the spy glass look around as there are really helpful tips and advice from our members
This topic for example Stand out elements in sitter applications? - #9 by Colin
Lots of information there … I hope not too much, take your time and it will happen. I’m sure your fellow community members will have some great advice also.
We are all here to help …