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. 

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.

What is the estimate for getting it rent ready?

Hi Eric,Great question—estimating operating expenses can definitely be tricky, especially for items like maintenance, CapEx, and make-ready costs that vary widely between properties.

Does anyone have suggestions for retroactively estimating your time? 

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

As far as whether to approach them with or without an agent - approaching them directly without an agent can save the seller probably 2.5-3% of fees, which give you some room to negotiate on the price, but you need to be confident that you are capable of evaluating the property value, estimating on the amount of work that is needed, knowing how to negotiate/ structure the deal, and navigating the closing process.

My estimate is 90% of the time we obtain a tenant in our first open house.  

Keep in mind all these markets are very different than the Cambridge area in terms of tenant base, household income, transit, etc.Happy to connect if you'd like to chat more!