However, 1. my calculated annual expense is lower than the listing agent's estimation.

When I told him my much lower assessment of the property's value, he offered to find me a lender who would finance based on the wildly inflated sales price.

If this one is lower than the other comps and you could fix it up to be comparable to the other comps, then it would be a good investment as you wouldn't be paying someone else's mortgage every month.

See if you can get a higher heloc loan with a lower rate with them and pay off the other one.

We are also looking to get in contact with a mentor that could help us get to the next level.

Below is some high level info. on how they work.  

I'm curious as to if it even makes sense to try and get a lower number or if the numbers work at the list price to just offer that.

I have a background in wastewater treatment, I also have some experience in multi level business. 

I wonder do you recommend a novice invest in lower cost properties to start?

I would much rather deal with a commercial lender because I would think that the rates would be lower.