It took my previous employer about one year to get his initial part 135 certificate. From what I've heard, you fill out pages and pages and pages about how you plan to comply with each little section of part 135, then send it to the FAA. 2 months later, they send it back with all the parts they don't like highlighted for you to fix. Repeat this process once or twice, and eventually you get approval.
I don't have personal experience doing this, this is just what I've heard. You might want to take a trip to the FSDO and talk to them about it.
Most FSDO's have an initial briefing with interested applicants. They walk you through the application process, forms, etc. You have to call and make an appointment to begin this process. Somrtimes there is a long waiting list to even begin this. The process for single-pilot is relatively simple, but is still very time-consuming depending on your FSDO location and workload. General Aviation and Single-Pilot 135 Certificates are way, way low on the list of priorities with the short-staffed FAA.
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