Well I have 5 mortgages and every one was a pain in the butt to get through because of my income.

Its brutally painful when my father has close to 60 units and renters work odd hours So my question is this, what are some good options for landlords who's tenants may not particularly be familiar with the Internet or smartphones?

That was a pain.

If a person is leveraged to the hilt, and they hit some bad luck, they will be in for some real painful lessons in finance 101.  

Sec. 207a.(1) ...A certificate of good standing issued to a domestic limited liability company shall state that it has been validly organized as a domestic limited liability company, that it is validly in existence under the laws of this state, and that it has satisfied its annual filing obligations.(2) If a domestic limited liability company or a foreign limited liability company authorized to transact business in this state fails to file an annual statement required by section 207 for 2 consecutive years, the administrator shall notify the company of the consequences of the failure to file under subsection (3).(3) If a limited liability company does not file all annual statements it has failed to file, and the applicable fees, within 60 days after the administrator's notice under subsection (2) is sent, the limited liability company is not in good standing."

I work as an auction administrator at a real estate auction company. 

I have 1 rental and it's a pain but it works.

We managed to pay off the loan by 2005.We bought our second rental in 2005, after taking out another equity loan on our primary, and again - - paid our "normal" mortgage payment, applied the rental from rental house number one towards the equity loan, made the normal equity loan payment and applied the monthly rent from rental number two towards the equity loan.In 2006, we bought yet another rental - using an equity loan on rental property two.That loan we threw the monthly rental money of the unit at.In 2008, we had paid off the note on rental number two and began throwing more money at the loan for rental three.In 2009, we bought rental number four and paid off the loan on rental number three later that year.In August of 2011, I retired from my job as a computer network engineer/database administrator at the age of 59 1/2, and began to withdraw money from my IRA & 401, using the losses on the rentals to offset the taxes on the IRA & 401 distributions.I had to use trial and error to guess how much to withdraw & be on the safe side as far as taxes go. $40K per year is roughly the "sweet spot" for that if you have 4 rental properties in the state of Ohio.

Having extra room in the budget covers one from painful unknown repairs as well, if having done all that -it still is profitable with hard money- then go for it.

I feel your pain!