I'm a senior .net developer and have worked on w2 and 1099. In 2009 I worked solely on 1099 and did about 1/3 of my billable hours for SaaS credit repair software company.
I worked with 3 other 1099 developers for this credit repair software company.
"The truth is, your system and processes are your secrets. Not your ideas or your code. Ideas are a dime a dozen."
I agree with this statement. All of us developers had access to the code, we could have done whatever we wanted, but we didn't. We were there to do something we enjoy, programming.
I worked remotely for this company and was pretty much available anytime for them. Unlike your typical w2 employee.
In 2009 I started my own e-commerce web site selling products. I have worked on many e-commerce web sites and decided I would create my own and sell products. I'm very familiar with our dedicated server, code, source control, database, etc..etc.. since I'm the one who set it all up.
If I were to start handing over some of the IT work that was involved with the web site, I would look for a 1099 contractor that would be able to dedicate the needed time to my web site.
I would start the contractor off on a small project and see how he/she does. I would go over the framework of the web site and show them the ropes.
After they have completed their first project, they would check in their code, I could review it etc..etc..
I have worked with a lot of developers all over the world and none of them have done anything malignant.
Make sure you have source control and backup procedures in place.
I have two part time employees and 2 1099 contractors. Paying them is pretty simple for me.
I trust them them just the same.
I'm an LLC, but next year my cpa will change it and file me as a corp. It will cost more for him to prepare my return, but I will save thousands.
It sounds like you have a lot of decisions you need to make. Maybe just start with one. For example, SEO.
I'm sure you are already familiar with your web sites current metrics. Possibly hire a guy or a firm for the next 6 months and see if there are improvements.
For me, I hired a company that just does backlinks. They have done pretty well and my rankings have gone up.
I used to do contract work for an SEO firm. I contacted them and they want $2200 a month for SEO. Maybe in the future, but right now that is too steep for me. haha