As we evaluate deals, we're wondering if we're being too conservative with our estimates.

Chances are they are paying others who are not as accommodating as you (amazing how people will make those car payments while jeopardizing their homes) - and it's time for them to move on to housing they can afford and to a tenant that does not require you to subsidize them.  

Before bigger pockets moved the rent estimator to pro users only it estimated rent to be around $975 I don't know or have anything to go by but I thought that was high.

From there, you can better estimate the end numbers and work back to figure out the GP/LP  equity needed and the estimated returns.

They care about what they estimate it would cost to rebuild the home.All else being equal, yes, older homes are more expensive to insure than newer homes for a variety of reasons. 

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

I hope you get the chance to visit someday; I’m sure you’ll love it!

I then created an excel sheet with those estimates to know (a) what to offer for land to make my numbers and (b) to hold the sub to what they estimated for me.  

Wanting to know who we can reach out to for management, estimates on potential income/expenses. 

@Jaycee Greene the estimated value of our SFH is $370,000-$400,0000.