I am looking for a property management software to handle online advertising, online applications, background checks, maintenance requests etc. all in one portal.  

Sometimes putting a for rent sign in front of the house works wonders and sometimes it can be detrimental to the investment itself.Why You Would Want To Use For Rent SignsRental signs are a great way to get word of mouth advertising from those in the neighborhood.

I sent an email to the state department as well to see what they say.I believe you would be ok and fall under the carve out provisions. that are intended for private investors.. they don't want you advertising or holding yourself out as a lender and the volume is like you describe a couple a year.. but you did the right thing check with the state. 

Best to advertise what you can do to help them in their current situation, then going right to $ or probate questions.

Did your advertising say $x for 4 people?

On the apartment building, a tenant moved out and the PM company advertised it for market rate rent.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has 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.

I've compared the prices to Pipedrive and other software I've used in my current profession, and it's been enlightening.I'm targeting property owners with high equity who have held their property for 15-20 years or more, and ideally with some kind of lien or code violation attached.I've heard that direct mail campaigns can be very effective, though I find that cold calling has always worked best for me in my line of work.

Can I advertise a product or service in it?

I want to start a publicaiton like For RENT or THE REAL ESTATE BOOK, or some type of home sales advertising booklet.