Looking for some experienced advice

Yea. Lot of good advise already given.

I personaly wouldn't consider putting on additional trucks untill you yourself have one truck running smoothly with steady work and a system for maintenance and admin work.

I also personally wouldn't ever own another truck besides the one I drive myself. My wife and I had 5 at one time and the stress level is NOT worth the 24-7-365 headaches. You will definatly not have more quality in your home life if you have drivers on the road. We run OTR weekly runs with everyone home 2 sometimes 3 days a week. It might be bareable if your hauling grain or something but do not advise multiple OTR'z. It's possible you have the tempermant to handle it but I guarentee it IS the heaviest load you'll ever haul. Hard to sleep nights wondering if someone might die in or under 1 of your trucks every night.

We are now back to owning only 1 witch I drive myself and love it. We do have 2 owner ops but o/ops are so much more dependable than company drivers as they're responsibility level is much greater. You can find some good company drivers but they are few and far between espescially if you don't have steady solid frieght. Nobody (well most anyway) likes floating.

My advice.....
1.Find steady frieght (preferably not brokered)
2.Develop a system for maintanence (hiring it all out can break yah)
3.Develop a solid system for admin and get fluent in all fees and regulations
4.work into expanding slowly

Remember; If was as easy as buying a bunch a trucks and going to work, everybody would be doing it.