Geez, that's what you get for getting quotes from a man and his truck and tools.

I had the epiphany today (I'm not a finance guru) why not take the equity to make this second rental purchase and do a smaller (condo maybe) in ski country and keep my rental.Part of the proceeds that I make each month from the rental pay my student loan debt and my truck payment so the proceeds from the sale were going to pay them both off and the rest would be re-investment capital.There is another part of me that thought of selling the the 2 family and using the capital to buy land and building multiple units up north or buy a couple condos.Are there other options I'm too much of a newb to think of ?

He tells me he sits by his from window, saw a sanitation truck come by, dump the garbage in the truck, some of it fell out, it was a windy day, so it got blown away and landed on my sidewalk.

A legitimate 2 man shop in my state with mechanic, helper, truck all the insurance and expenses runs around 150k/year.

Moving truck or plumbing truck in the driveway? 

There are legitimate reasons to inquire about the truck; no one said otherwise.

Sure 1  McDonalds sells 4,000 Big Macks a day for $2.00 a piece, sounds like they are taxed on $8,000 a day, But the truck to drive it there costs, the burger costs, the lettuce costs, the franchise fee costs, the employees and their employment taxes cost, the lights cost, the driveway pavement costs, the water for the bathrooms cost, the depreciation for the new chairs cost, the land tax costs.

His truck broke down somewhere and I towed him back to my house so he could change the rear axel with my tools. 

Then hire a construction company, with vans and prominently displayed contractor license numbers, NOT a dude in a truck, to give you a real estimate on the basement.

They used an example of a truck leasing company, but the point is the same: if other people pay the loan, other people grow your bank and you benefit.