Our technology platform services provider has to do them manually and we are looking for a solution. 

This is done using blockchain technology such as Tezos or Ethereum.

Even tbe quality of property makes a difference Lower income can be challenging because they are paycheck to paycheck, might not have technology to pay online, or if it's a bad area might attract bad people.

Though the statement from one of the firms suggesting flippers had an easier go during the GFC than long term property holders is laughable to me.https://www.nytimes.com/2018/09/27/technology/next-techs-agenda-real-estate-opendoor.html

I have a good ability to turn technology concepts into business concepts, reflect what it means financially, and present that information. 

A heat pump is used as an alternative to gas, so your concern about electric base-board heat is invalid...the entire heating system would be electric...Heat pump technology has come a long way and these things are good at providing heat to a property with a 3rd floor as long as your ducting is good...and more importantly, your R-value...I would look at 1)- better insulation, 2) extending the gas line and adding a gas furnace, 3) installing a PTAC unit, 4) Installing a mini split...or baseboard heat...its actually a really good heating source...and think more about hydronics...in my opinion hydronics is absolutely the way to go in almost any situation with boiler technology...Best of luck. 

Do one or both for the education and modify as you learn and build wealth -one thing for sure is it is not static  it changes with age, health, laws, technology, family situations, etc   Taxation, succession plan, estate plan, insurance etc may all play a role.

If they aren’t technologically savvy I then let them mail me a check.

@Joe GrazianoI don’t know if you found your answer or not but from a technology perspective, you need to get access to the MLS API and obtain a key to which could feed data to your site.

Just look at this forum itself - a (fantastic by the way) piece of technology built by real estate investors.Would love to connect with you as a fellow developer!