We purchased it with a conventional loan with 20% down and we estimate that we already have about $200K in equity.

Most Insurance companies have estimating programs that calculate the amount needed. 

We did try to get one group to do it all, but they never got back to us with an estimate after visiting the job site.

If they send an estimate over and I think I have a better option, I'll let them know I'd rather send in my resource.There's a lot to cover, so it's tough for a PM have both a deep and broad deck of resources all the time.

They should be providing you an estimate with breakdown of the total fees to close the sale. 

You will get good enough that you will be able to run these calculations in less than 2 minutes for a ballpark estimate on a house you are looking at.  

So some basic numbers on these homes:Total estimated value of all homes including their primary home: 5.8MTotal remaining loans on homes: ~900kInterest rates on these homes range from low 3’s to mid 4’sSo two questions: 1) Do I need to cash out refi each individual home if I want down payment money or can lenders lend based on the entire portfolio?

Not allocating cap ex and maintenance because an item is not expected to fail soon is simply providing a misleading return estimate.  10% maintenance/cap ex ($132) is less than half of reality and maybe less than 1/3 of reality.  

We generate the leads and manager would need to convert, estimate and see it to close.  

I have been trying to estimate this for my clients, so it's great to have this to reference.