I've made my fair share of mistakes, but refined what I do into a perfect  system.You need to remove the word "risk" from your vocabulary.

Sounds like they didn't counter-offer... they accepted your offer.Feeling nervous is perfectly normal!

So here is the question: if you were looking to build a portfolio of 50-100 SFR, you have 2 great W2 incomes, perfect credit, and $50k to start it with, where do you begin?

We have encountered companies which will not underwrite knob-and-tube or aluminium wiring {which can be perfectly safe}, but never one that refused paper/fabric-covered wiring.What does your insurer classify as "fabric/cloth covered wiring" {I cannot really see the pictures closely enough).  

Another consideration with the 10 acre example, imagine it being a perfect sqaure on the map for illustration purposes.

When you decide to turn it into a rental, you go rent for 3 to 6 mos until you can find another perfect house to buy owner occupied.

You're the perfect person to be able to keep ongoing maintenance and cap ex costs to a minimum!

Our old W/D were perfect for the rental unit.

@Peter Vroom Ahh, perfect situation where slumlords get their slums.

Your suggestion to stress test makes perfect sense.