While I know this was unusual and over the top, it gave my wife and I the confidence to go ahead and pull the trigger. 

It's an investment you make once and will be able to confidently use them over and over again going forward. 

Generally, I'm looking for a duplex that I can be reasonably confident that I can rent out for at least what it costs me every month (principal, interest, property taxes, home insurance, mortgage insurance), and hopefully a bit more.And generally, anything else I should be thinking of?

I found that my past experience in these types of properties as a former licensed plumber and a 19 veteran mortgage banker has given me the experience and confidence to improve the performance of the project.

Initial estimates put ARV at 95-110 and rehab at 15-30k (less confident on this).My two questions are...1) As a wholesaler, how do I go about getting this under contract, before they decide to list with an agent, and at a number that makes sense?

Look at this guide to get a good idea of how to do valuations:https://problems.com/resource/real-estate-investing/As long as you see better deals that meet your criteria, with enough safety, you will feel more confident in pulling the trigger.

I want to jump back in for another project, but I probably should wait for a couple months. 1 to let my wife gain some confidence and 2 to build a little more cash.

Perhaps, having someone with boots on the ground in the area that you want to invest in, who can verify your contacts, rehabs, take pictures and be an added layer of confirmation for you, could help ease your worries and strengthen your ability and confidence to invest out of state.

The good news is that it gets easier and easier with each call you take and your confidence will build. 

I have some cash and a heloc I can take out, also some family that has committed cash as well.I am having trouble finding the right deal mostly because I am not that handy and don’t feel confident with a major rehab.Any leads on a good wholesaler in Cedar Rapids to help me find my first deal???