My gut says there are better opportunities out there so I would pass, but if you continue to pursue it, I would encourage you to be extremely conservative as you underwrite this deal.

Make sure to conservatively estimate the expenses on a given property. $10,000 will dwindle very quickly if it is a problem property or you simple don't forecast costs accurately.

I like the idea of the thermal camera, but get an energy audit from a conservation professional.

I’d make sure (and I’m sure you’ve already done this) that you’re being conservative with your valuations.

@Brant Biba I know this is general but Dupage County makes for a solid conservative long term buy and hold.

While it seems appealing in other markets purchasing a property solely based off a higher cap rates, one thing often overlooked is appreciation in our NW region. 3% is our conservative start but some areas are seeing much higher.

Since I was in no rush to purchase the home, I gave her the number that worked based on my conservative analysis and waited for her to come to me!

I always run numbers very conservative so worst comps (provided by my realtor) and highest rehab costs (minimum of 5 detailed quotes) will be a good starting point for your deal.

Making entire business model more conservative for projections, timelines, etc

Start with something that resembles what she's use to, less work, less hands-on involvement, yet comes close to what she's seeing in her stocks on a monthly basis.Lastly I would ask her to do a mock REI portfolio with you, find a property online, if needed do a mock rehab on it, rent it out at conservative rental rates etc... maybe this will let her see that you know what you're doing without initially taking the investment risk, just be conservative on this because if your Mock portfolio fails it's over getting her to say yes.