Yes it is possible to make clear that much with 5 trucks. It depends if they are in town routes or if they are long hauls, and if they are turning two shifts per day.
Fifteen years ago, a ground city driver told me they got paid per stop and their pay increased with the distance from the yard. The over the road routes are probably more steady.
I have a friend of a friend that got into this three years ago and has put three routes up for sale for $1.5 million. It sounds like a great deal to me. If you can net about $80,000 per year on one day run...I would do it. After getting it paid off, hire someone to run it, and then use that to supplement my retirement income.