Young professionals are not going to have old outdated electronics and will most definitely know how to connect to the internet and navigate the network.

This includes solicitation of donations by or on behalf of charitable organizations;"The grey area comes in the fact you are "promoting a service".The only clear-cut exemptions from the DNCR are:  Canadian registered charities;Political parties, riding associations and candidates;Market research polls and surveys;Newspapers of general circulation for the purpose of soliciting subscriptions;Telemarketing calls from organizations with whom the consumer has an existing business relationship are also exempt (a transaction has been executed within the last 18 months);Telemarketers to whom the consumer has granted their expressed consent (written form, electronic form, or recorded verbal permission). 

I obtain the binding signatures electronically, via Adobe EchoSign.

I have some rentals and they all pay electronically so I never get any mail from the rental.  

I am an audio electronics technician (and musician) so I'm always calling my customers to discuss pricing and what repairs their amplifier or guitar needs.  

Purchaser has option to pay off after year five (5)A single purchase price and financing term must be elected by both seller and buyer before the LOI is effective; the above terms are customizable to fit the tax and financial desires of the seller. 1)Insurance Documents 2) Environmental Report 3) Property Condition Report 4) Previous Title 5) 5 Year Loss Run Report 6) Rent Delinquency Report 7) Electronic Building Plans (Any) 8) Past 5 Years Major Capx 9) Previous Survey 10) Current Rent Roll 11) 3 Years Trailing P&Ls 12) Property Tax Bill 13) 3 Months Utility Bills 14) List of Personal Property 15) Copies of Service Contracts 16) Access to All Leases Deposit: If there is a balloon payment in year one per the respective price and financing terms, $5,000 initial deposit will be paid to Seller within 3 days of effective date.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

"Mailing list" also includes a magnetic tape or similar device used to produce written or printed names and addresses by electronic or mechanical means.IMHO you will be fine

But, I'm thinking about  handwriting the name and address on the envelopes, with a real stamp (not electronic). 

It's a bank account with a banking app that is essentially just an electronic "envelope system" but it allows you to categorize transactions from every swipe and then credit that expense from the appropriate envelope.