I would probably only enable Dwolla and Stripe.

It probably is not past the statute of limitations (20 years since last payment), but two things might happen that could enable you to succeed in getting the mortgage removed from the title by court order.  1.

Having positive cashflow enables you to fund reserves and to hold on to the property indefinitely which gives you time to allow the magic of leverage, appreciation and debt pay down take effect.

@Robert Biggerstaff, it’s a really interesting question and touches on a few key topics.1) You likely need to be active to start with and to build up capital but in order to scale you have to automate, delegate and systematize your active pursuits or take a more passive approach by investing in others deals2) Setting a pure financial goal is a good start but it can be even more powerful to state your goal in terms of what it will enable in your life I.e. what will happen when you hit $50k a month, will you then not be happy until you are at $100k per month.Good luck!

That way I could take the proceeds and roll it into multiple other deals which would diversify my risk and also enable me to continue compounding returns.

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I aim to use real estate investing to build generational wealth, enable me to work a traditional job only if I want to, pay off my student loans, travel on demand, pursue dreams and to give money away to worthy causes. 

Section 8 adds a standardized lease, annual inspection and a subsidy to enable the prospect to afford your rental.You and Tenant sign your lease and the S8 lease. 

Doesn’t that make it impossible to get the full 15% step-up in basis enabled at 7 years?  

I know you have extensive management experience but perhaps that could be a compromise that will enable you to keep pursuing RE investments but not place so much stress on your husband?