Andrew, you have been doing a lot of thinking. I would say the first thing to do is pass the CDL test and get your license. If you can save $20,000 why not use that money to pay cash for a truck? It is much better when you don't have to worry about making truck payments.
1. I prefer a corporate structure, but that is just me. There are some tax
advantages in having things set up under a corporate structure, but
every situation is different. You may just as well having a
proprietorship. With one truck, it is something you may want to run by
a CPA or attorney. Either can better advise you about that and your
needs.
2. I am not sure why you would need to use a payroll service. Most
companies don't use them unless they have a lot of employees. You
could use Quick Books or Quicken. There are software packages
specifically designed for the professional owner operator. One is
trucknpro by foglinesoftware. It doesn most anything you want but
payroll and fuel taxes. If you lease to a carrier that won't be a
problem. Easy Trucking also has a package and it does the fuel taxes
at twice the price of the trucknpro. If you want a trucking package that
has payroll then Truckers Helper is a fairly decent program. Or you
could just use a spreadsheet.
3. The best way to find an accountant with trucking experience is to ask
make some telephone calls. OOIDA had at least one listed on their
website and may have some listed with Landline Magazine. You can
also check in some of the trucking magazines and the Truckpaper.
Some advertise in them. I prefer dealing with someone locally. It is
usually good to have a lawyer you can trust when you need one. You
will have a contract if you lease to a carrier. You don't need to have a
lawyer to set up your corporation, but you might want to run the
structure up with one.
4. OOIDA is about the closest thing we have to a trade association.
Membership is open to all professional drivers, owner operators and
independents.
5. OOIDA is a good resourse for most anything you need as a driver or
owner operator. There is usually someone who can answer your
questions.
www.ooida.com.
6. I prefer flatbed freight. I like to be outdoors, get a little exercise and
the money is usually better than pulling a van. However, never do ANY
job strictly for the money. There is more to living than working at a
job that you dislike.
7. I believe you are talking about freight lanes, not trade lanes. It
depends on the time of year and type of freight hauled. For the most
part anything East of I-35, West of I-95, North of I-10 and South of
I-80 is considered the best area for freight.
8. Hub or practical miles are closer to actual miles. I am a little different
in how I run, since I run my authority. If I were leased to a carrier I
would look for one that has good rates and pays percentage.