This allows me to do a 1031 exchange and get into newer properties with better tax advantages (once I have used up most of the depreciation from the previous rental), and it allows me to never deal with deferred maintenance issues that increase my cost of ownership.

Never mind the fact that there are a whole lot of people looking to buy a property (increasing by the day) to live in themselves.From what I have seen, most MLS listed duplex properties in Denver (and most other properties, too) are at a purchase price that would put you so far away from the 1% goal - it would be impossible to cash flow them now or in the near future. (1% being the rough guide for considering a property, rent/month is 1% of the purchase price of the property).

Let's rounded to $400/mo/unit to simplify the numbers.That is an income of $1600*12/yr from rent ~= $19,200Now, expenses:Maintenance: $9,600/yr (50% rule)Taxes: Around 1% ( lucky New Mexicans): $1,700/yrMortgage Payment ([email protected]%): $763/mo ~= $9,150/yrInsurance: Around $1,000/yrPossible Cashflow per Year: 19200 - 9600 - 1700 - 9150 - 1000 = (-$2,250)A negative cashflow does not look so good, but here are 2 opportunities to increment it:1) Increase rents.

@Simcha Davidman seek for a local wholesaler and learn the trade, you will get the best deals that way, I agree with @Judy P. when she suggests to start with Single Family, what if you really don't like being a landlord of one family, how will you handle multiple? 

Beyond that, I am intrigued by the possibility of building a portfolio of small multifamily properties and generating cash flow to increase my flexibility and time with my two young sons.  

The other part of wholesaling that is a possible red flag is Equity Stripping, AKA Illegal Flipping, this was heavily regulated till a few years ago by lenders, especially M.I. companies, they have relaxed the rules, but was a problem pre and post crash. seeing the increase in this activity seems eerily familiar,  like 2007 all over again. just be careful especially with your license, Disclose Early, Often, and in Writing, My license is too valuable to me to be involved in this type of transaction, so i steer clear. if my entity is on the contract, I am the one closing. period. 

I would like to start keeping books on my properties vs having their financial information buried in my personal finances.My questions for the community:1) If my goal is to eventually seek financing from others and therefore I will need P&L Statements and other reports on my properties, what software should I use - Quickbooks, Buildium, etc?

Therefore, you can't sell the home to yourself to increase the tax basis.  

A quick mls search shows the cheapest apartment rented in Framingham that was listed in the last 6 months was rented for 925 and Ashland $975 so it looks like you have room to increase rents if your building is in decent shape.  

@Jose Jose, glad to hear you're thinking about this- water savings are an amazing way to increase your return.