I'll paraphrase an ancient saying, "he who holds the gold, makes the rules."

Funny @Brian Burke, I was thinking they must have skipped over Leybovich's guest appearances ;-)@Joshua Dorkin - the acknowledgement looks good on you.

I negotiate all debt that are in this status. 

I am seeking to 1031 out of the rental and into a 'mixed use' property consisting of a main house that we live in and then a guest house that I would either rent out for 1-2 years or use as a business office for an established business that I've operated for 5-6 years and paid taxes on, etc, etc.  

A lot of times being a landlord it is about minimizing your exposure to liability.If a tenant or their guests or kids were to get hurt on the property, you can easily expect yourself in today's society to be involved in an very costly and possibly very long lawsuit.We advise owners not to leave on lawnmowers, ladders, weedeater's, yard equipment, or even cleaning supplies and chemicals.

LOL this is gold.

Currently I have a single one and am looking to acquire a 3 or maybe 4 flat here in Chicago, or another couple of properties in Kentucky.There are a few things l'd like to have:Tenant portal for announcements and service requests / status bits and paymentsMisc expense tracking of consumables for a property for maintenance and general upkeepTrack recurring costsSome tools to visualize the cash flowsI could do it manually, but know it would be possible to, for a given property, generate more or less the total ROI ie: "Over the past 4 years, this property has paid for itself and generated $YY in income" or maybe "When full, this 4 flat generates $ZZ worth of income, but averages $BB in expenses due to maintenance", etc.The other option, which I'm entirely comfortable with (I'm a software engineer by trade and have worked in this industry for 10+ years) is simply writing my own and likely then open sourcing it (aka giving it away for free).What are everyone else's lists of "must have" vs "nice to have pony features"?

Regardless of your lending status or the types of loans you offer to the public, when you have an applicant apply your fiduciary responsibilities begin as a lender. 

If you do set up your own simple website, you will then have to constantly update your rates and calendar so that you can provide the potential guests who go to your site real-time information.

Tenant agrees to pay for repairs of all damages that they or their guests have caused.