Don't buy trashy properties in suspect areas from afar thinking you can turn it around easy and make a big payday.That is frequently how many lose their shirt and go back to investing where they live with their tails between their legs.

--sticker stamp, metered mail, media mail stamp, etc?

I recommend 4x6/5x7 (invite) envelopes, and creative stamps to appeal to the seller and separate yourself from the rest. 

Some municipality requires a transfer stamp in order to refinance, and to get that stamp they might require an inspection. 

I know lots of people who lost their shirts because they could not make it through the troughs, got margin calls when the market tanked, and they lost their home and any savings, while others were able to weather the storms by being more conservative.The statisitics gatherers will tell you that prices only went down by 25% between the highs and lows; but in the lows there are no buyers of SFR’s, so houses would sit for a year with no takers-few can stand that.

This is going to be especially true for students, who these days have so much debt they don't even really own the shirts on their backs. 

Deal analysis is the primary source of value creation/delivering returns vs. losing your shirt.

It would save buying a money order and licking a stamp and envelope.

Right now we put dates on each but I would love it to keep track automatically based on when we update the "status" to the next phase.It would be great to have date and time stamps as well as who entered what ie so we can see who turned on utilities and when or when they were turned off etc.

At a minimum, send them an invoice each month 10 days before rent is due with a self-addressed stamped envelope.Visit your properties or have someone else visit them on your behalf every couple of months.