I am looking for the best and most cost effective software for the following needs:-ACH rent payment and rent payment tracking-Lease expiration tracking-Maintenance costs by property-Maintenance requests by tenants-Document generation for a small amount of documents (lease amendments, late payment notice, etc.)

I cant tell you how many amendments we have had to do for clients who wanted to do it themselves and lost 5 figures + in tax savings 

If you dig further into the IBC (and associated Massachusetts amendments per 780 CMR), then you will find the requirements for a sprinkler system to be added for such a conversion or new construction in a three family.

I'm usually not competing for the same customer as the large multi fam properties, and so my rent market dynamics are different (and hopefully more amendable to rent increases).

@Randall E Collins One way around the assignment is merely draft an amendment to the original contract with the agent stating "Buyer and Seller agree that XYZ (your end buyer) is the buyer" (or word it how you all agree) BUT have an email with the end buyer and the closing company stating what your fee is first to secure your fee. 

., they may have amended the ordinance.

Worst case I’d send out a simple addendum…The lease agreement between landlord x and tenant x is amended in the following ways.

I have clients that are currently amending taxes because their previous CPA didn't understand this industry.

HaleyThere are different ways this can go. 1) if you acquired the property in the current year, you would put the assets in your depreciation schedule just as any other asset and take the benefit of accelerated depreciation. 2) If you did a retroactive cost seg, you have to file for 3115 and take the adjustment as section 481 adjustment3) If you did the cost seg on the properties that were acquired last year(only one tax return has been filed), you could amend your return from the prior year. 

@Timothy Taylor, Obtaining the Zoning Map Amendment (Zoning Change) to RT-4 now "Permits you" from a Zoning Standpount to "Add" the 4th Unit (Assuming you have at least 4,000 sq.ft. of Lot Area).