Then see what they paid for cleanings, usually it’s a pass through expense.

The new owner bought the house after I purchased my land, and he might not be aware of these encroachments.Is there any risk for me, such as the possibility of acquisitive prescription of a part of my real estate after years, especially if (theoretically) the neighbor incurs considerable expenses for e.g. asphalting his driveway? 

Both have income and expenses and a NOI.

Property is so expensive that if I were to put 20% down here that would be $300,000 for a 1.5M multi family which is what I've been seeing for any decent place in an area I'd want to live.

Determine the rent you need to cover your expenses and then add the desired cashflow. 2.

Some of the things I'd like it to do/keep track of:-Track purchase price, details of any loans, and current equity in the property as well as total portfolio equity-Track current and past rents for properties-Track total ROI for individual properties, as well as entire portfolio-Track expenses, be able to upload receipts, bills, etcAny suggestions are greatly appreciated. 

And someone jumping into this as a complete newbie can expect that they have a decent chance of making some expensive newbie mistakes.

The wholetail is a smart play, but you should be cleaning the place thoroughly and doing no repairs and then presenting an honest proforma with rents and expenses estimated so investors have a PDF to look through.

Accounting for approximately $10,000 of repairs, maintenance, and capital expenses per month, this still leaves a passive stream of about 20,000 to split between two partners.

Hiring a bookkeeper to watch the income/expenses is like hiring a gardener to tell you how many roof shingles are laying on the ground after a wind storm instead of hiring a roofer to repair the roof.I recommend that you look for a quality property manager who can maintain the properties and help with the bookkeeping.Start by going to www.narpm.org to search their directory of managers.