Thanks @HappyDeb ! Yes, I’ve already begun copy/pasting previous application letters, then just updating/editing according to the human/pet/town, etc - so that is definitely helpful! Thanks for the tip!
I think everyone is totally on the right track here. Since my original answer above, I posted dates for another trip I’m taking and got two applicants almost immediately. One is new, with no sits or reviews yet, and wrote a medium-length paragraph describing what kind of housesitting she had done in the past, why she was returning to it now, and explained that she works remotely. Her message may have been a template (there was nothing totally specific to my listing) but informative. and at least addressed me by name. As it happened, I had just confirmed another applicant who had already applied, but otherwise I would suggested a zoom call and she might well have worked out.
The other was a short generic template message “I believe I would be the perfect fit for you…I look forward to hearing back once you’ve reviewed my application…” I wasn’t sure what she meant by ‘application’ - her profile? - and there was no elaboration why she thought she was a perfect fit. It felt - fairly or not - as if she had not put much effort into reading the listing or provided any compelling reason I should consider her. I declined that applicant with a short “thank you, have just confirmed another sitter, best of luck” message.
All of this is just to say I agree with everyone above - having the message personalized to my sit is what’s most important to me, the length is secondary.
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Not good, definitely not, but another classic example of a sitter rushing straight in to get into the first five. The second “application” was definitely not good, but some sitters are doing whatever it takes, just to get in on that number five and hoping, on the off chance, that it just might work.
That is a good point. I hadn’t thought of my location (or the listing, for that matter) as so desirable that people would be rushing to apply but you never know what people’s reasons might be - they could have relatives in the area or something about the timing might be important. I should have added that I did also read the second applicant’s profile and they looked like interesting people but not a fit for my sit for a number of reasons. I guess more accurately I think of it it as, an unremarkable application alone wouldn’t disqualify an applicant for me, but a personalized application is a plus from the start.
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Thanks for broaching this question, and thanks everyone for this input! I’m brand new to the site and have applied to about 20 London sits in the last week, and have gotten 7 positive responses (even in the case where they didn’t book me for this time but wanted to stay in touch for future).
I have been doing a super simple intro to be respectful of everyone’s time, and because I spent a lot of time and effort fleshing out my profile and figured people would explore there anyway. Much like dating profiles, I also wait until a chat or video call to get a real sense for connection 
. I’m also exceptionally well-qualified for pet sitting so felt that showed in my profile.
The input from everyone has been super helpful to guide me for the future (though I have two sit offers now!) - there were many instances where I had a personal connotation to the pet or location but didn’t share, so I’ll wax a little more poetic in my future outreach 
Like @Marion wrote, in a competitive area it might be smart to write a short message first to apply.
I have had applicants who wrote a more basic note to show their interest first and then sent another message with more detail - like that they are traveling around in Europe and would like to visit the area we live in, why they would really like to take care of our cats and home, and what their sitter experience was.
When I choose my sitter I usually take the first one that seems to fit and arrange a call with them. If there is one application and I like what it says I pause the application process. That way, if the person who wrote first is suitable I don’t have to write to decline other (maybe also suitable) applicants. I always feel sorry for the people that have put effort into an application but I have to decline.
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No, I would only accept a short application like this if the reason given is the 5 applications rule and a longer one follows.
I don’t want to scroll through lots of profiles just to find out that the sitter isn’t what I was looking for.
The application doesn’t have to be exceptionally long but should cover more than just hi and look at my profile.
Edited to remove personal information
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