OP: I can't speak on behalf everyone out there, just from my perspective. When I post a job on upwork, I invite 20-30 people from the lowest price range, because in my experience they are just as good as the expensive offers. For example for the same javascript development I got $5000 and $150 offers and guess what the $150 person actually seemed more experienced and knowledgeable than the $5000 based on the questions they asked about the project.
When I chose who to work with:
1./ I give a fuck about the cover letter, everyone is lying there, promising everything, just to get the job.
2./ I pay more attention to those offers who message me. (faster is better) The reason is, that I see the messages immediately, while to see the offers without message, I have to go to the proposals menu. That is more effort, sometimes I even forget to do that. Be the first who they notice, by sending an extra message, not just your proposal.
3./ I select someone with low prices (sorry I am cheapskate)
My advice:
Ask questions from the seller so he can feel that you care about his project, you want to understand him what does he want. An example:
For the mentioned javascript job description was very vague it didn't have any details what the work is. One of the sellers immediately asked for $1200 without even knowing WTF I want. Another seller first asked me for the details, clarification, etc, and then offered me a price. Most of the buyers are afraid that you don't even understand what they want, because you might from another country, culture etc. Make them see that you understand clearly what the job is. People like those sellers better who care. Don't just send your offer, but make them feel that you care, and you want to deliver the best for them. Without asking them questions it's not really possible. Again, these are sales and marketing skills, not graphics design skills.
