Like the thread opener asks, what's the best way to approach the business (paraphrase).
I've been able to do contract, have employees and run my business as a solo operation. Mostly, especially in the last 7 or 8 years it's been solo. That decision was part numbers and part lifestyle choice.
Lifestyle: Elizabeth and I don't have kids. We're both self-employed. We like to travel. When I DO work, it's often right up until evening, and like I say, getting out in the morning is sort of a 'whenever'. I could go on and on about the joys of the freedom of working in an employee-optional system, but I really don't recommend it for most. Now, I'm speaking to the noobs here: Probably a better route would be to have an employee, and a light dusting of solo jobs, simpler ones, for when employee is not available, but you're working. You could have two employees, but now you're pinned to the wall to keep jobs on the books. This however, will have it's issues. The noobs are really wanting to develop a plan of intent, an approach to their climbing career, asking of our experiences so they can seamlessly weave their own.
Numbers: An employee is supposed to relieve you of some of the work on a jobsite, and make you more money than he's costing you. Employee costs start with wages, but ripple outward to things like his insurances, workman's comp, employee taxes, the paperwork, record-keeping, bonus pay, buying him lunch when he shows up without, having to purchase and keep extra PPE. You assume the risk of his injuries on a jobsite; if he gets hurt, it might not be your fault, but it is, ultimately, your responsibility. Being a taxi driver, a banker, a counselor, increased gear and tool maintenence. Then there's the days when he shows up late, you wait. Out doing estimates and he sits, getting paid and your income flows backwards, days when he calls in wanting the day off and your day is scheduled around having help, days when he's in a funk, and you're on a mission of completion. Then there's the days you want off and he's therefore stuck for the day without work or pay. Communication eats a lot of productive time. Many guys will take a break when they need one, and that's fine, but they'll also be compelled to stop working every time YOU stop working. Cigarette smokers have a need to break more frequently, otherwise, after enough time, they can get rather crabby. Some guys are simply not motivated and self-directed and need constant instruction. I'm not so good at that after the first week.
When you're the boss, employees depend on you for a lot more than just a paycheck, and you have to either assume that extra weight, or fire them. I hate firing a guy, even if he's not working out. Over time and experience, I found having an employee generally gets me through more work in a day, but I come home with equal or less pay. That is why I prefer to just work alone. Same pay, less stress, less responsibilities, less time and work outside of work. Overall simpler logistics.
Is that enough? Every tree operation is going to be different. Solo operations are definitely not the norm, and I would dissuade noobs starting out solo, for safety reasons more than anything, but technically you should be rather competent and a good problem solver.
I'll close by saying I have had groundguys that I'd do about anything to have them back.