I was hoping to get some shared insights into what the best starter tech stack looks like for a wholesaling operation.

It really depends on your specific situation.It's good you're thinking about the operational and bookkeeping component for your financial account structure to make things easier on yourself and any financial team members you have or may have in the future.You're ahead of the curve!

We dispatch them first at $50/hr to see if there is a simple fix and there most often is.

As Remington mentioned above, I would be cautious while wholesaling since so many wholesalers try to go around without disclosures and simple contracts.

For BP readers in NC (or other trustee states), get to know the trustees that operate in your county of choice, then periodically look for upcoming sales.

Living, but either way you could try speaking with existing owner/operators groups in the greater bay area, or even central coast, looking to expand their portfolios for a joint venture.  

You're essentially buying into a partnership with your friend with the partnership owning and operating the property.Now, the financial side of that gets more complicated and would generally include an advanced proforma/financial model that includes a GP/LP equity waterfall schedule that is based on how you and your friend agree that you will pay her and also share the profits.I assume that won't make sense to you right now, but I'll send you a DM.

I realize there is probably no simple answers but I am all ears from all sources. 

I ran into this recent TurboTax article  that led me to believe it was possible: Second, you may have a net operating loss (NOL) if the Section 1231 loss is large enough to reduce your other income below zero.

Ditto @Michael Baum - a simple 3 ring binder and I update/replace it if it looks even a bit worn down.