Software Development background here too!

Forcing them to pay online using your software or paypal could be a better option as well. 

That’s the way the accounting software works.

Very cost effective and the software is free from them.

Along with the uncertainty of the Covid 2nd wave, it will be interesting to monitor closely. 

@Jeff Hedfors, the IRS actually gives you a safe harbor that allows periods of personal use of up to two weeks or 10% of the actual days rented - not including residence while working on the house.So your period of residence while putting it into service (or monitoring the snow removal company periodically) is  fine.

Ideally there would be some way to identify the following characteristics:Duplex - Fourplex allowed via zoning (though around Houston we lack zoning), also without deed restriction preventing duplex builds (where community says what is/is not allowed)Dimensions - Ideally 100-150' frontageSquare FootagePriceFlood zone (ideally 500 year+)Neighborhood stats (Crime, School, local storesShould it be as simple as calling a bunch of agents/land brokers and saying what I want or is there a data/software package I can buy?

We'll adopt technologies where there is a strong potential value, but that value depends on the specific business you're in.There's plenty of technology out there that we use in the multifamily syndication space, anywhere from CRMs to demand-based pricing software to determine rents based on real-time demand in the market.

I am a software developer by day and I work from home. 

@John Zavala It could be a glitch in the software.