I am employed full time in software sales, and my wife is full time employed in Digital Marketing. 

I think the best one for what you specifically described though and for the size of your business is NowRenting.For $9 per month, it allows you to streamline those processes such as:Posting your listings to multiple websites at onceSetting pre-screening questions & automatic scoring of tenant leadsFree eviction, credit and background check reportMonitor the status of leads and tenant requestsSending digital rental applicationsCreating, sending, signing digital leases (w/the ability save, re-use & edit the templates) Collecting rent online (tenants can enroll in auto-pay, too) and delivered to your bank account via ACHAccepting & managing maintenance requests onlineAutomating notifications to tenants (rent due, rent late, eviction in process, etc.)Centralizing all communication (get a NowRenting inbox & phone number to keep your business life organized)Manage your properties from a mobile app or via browserCreating an easy custom website for all your propertiesIntegrating QuickBooksHope this helps, @Frankie Clark.

Also, you could consider one of the digital monitoring systems that are really cost effective (I believe there's a company that is a sponsor of the BP Podcast).

Interested to hear from anyone who has bought an existing website as an income play. Technology is my business, but I have never been on the buying / investment end of a web property. My questions:- What kind of analy...

I guess I am spoiled with cap rates in double digits.

Unfortunately, we are now transitioning to closing down operations.Personally: I have a whopping 6-digits of student loan debt.

@Yulyana Karpava find a market that will net you double digits, then find a team that will look out for you .

The targeted reach, cost per acquisition, budgeting, speed, metrics ... there's a reason billions of dollars are poured into digital marketing daily.I like to look at marketing from the perspective of: What would catch my attention as an investor?

Double digit net caps are to be had Good Luck 

I hope to start virtual wholesaling and want traffic to have a digital option.