First of all I disagree with financing. Sometimes financing is good so u keep cash flow available for emergencies. All depends on your situation. Regarding insurance don't hire one single employee (even if u pay them cash) until u get workmans comp, regardless if required by your state. Our 1 st employee sued us and got $30,000 and won ( probably wanted more but that was settlement not including legal fees) plus he got and was able to keep several yrs of unemployment!! We had insurance thankfully!
Not to mention the liability insurance etc.
Regarding putting mower in back of truck, where will u put debris? It's unprofessional to put out to road at customers house.
Try buy used equipment and consider training on how repair equipment yourself, or maybe u are handy already?
Lastly consider advertising if you are ready, message me if u need help. I have high ROI on direct mail!