Updating Commercial PM Systems from "Mom & Pop"

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I am looking for advice on updating some systems with a commercial building I help manage. Basic intro - I starting working for a local investor/property manager in my small town as a kind of personal assistant. We manage the biggest building in town (roughly 26,500 sqft and 20 tenants), but it's run in a pretty informal way. Our goal is for me to take over management of the building completely so that my boss doesn't have to bother with it. I'm brand new to real estate so still trying to figure out systems and everything else. 

One thing that is a little clunky are managing invoices and reimbursements for maintenance. Currently we just save the invoice in Dropbox and edit a Word document to add up the invoices, and send it all over to the accountant. We have multiple accounts that may be used to pay for maintenance/supplies, though, so we have to keep track of who/what account paid what invoice and reimburse appropriately.

Keeping track of rent roll is just done with an excel spreadsheet and updated as things change, which inevitably means something is missed or not updated correctly or in a timely fashion.

I know I can't explain everything that could use a good process re-make, so I thought I'd just ask how others are managing leases/rent roll, expenses/reimbursements, and anything else. Is there software people are using? We "use" Asana for some things, but that's also part of my role is to figure out how we can implement it better (there are three of us). Anyway, just looking for some tips and tricks for different systems and organization for management of a building like this.

How many units does the company manage overall?

Yardi is pretty expensive, so may not make sense on only 20 units.

I will look at Yardi and Buildium. I'm thinking at this point Buildium may be a better option simply from the cost standpoint. @Drew Sygit At this point, we only manage this property and we are rehabbing another property that will only be 4 additional units. 

@Jai Reddy I'm curious to hear why you started using Excel instead of Yardi and any ideas or processes you have with Excel. Do you have tenants email maintenance requests or ways you prefer to manage those things?

For a commercial strip I manage, with about 8 Tenants, I found Excel simpler (and free). There was a template I downloaded online and modified it to my liking. All I needed was to track income (rent payments) and expenses by month, and then have one summary page I can submit to anyone requesting for financials.

It looks like you want to manage it well, but the enterprise level solutions (yardi, appfolio) are too expensive. From what I know, many commercial managers aren't doing management well and adding big expense might hurt.  Check out ManageCasa, because it's good for small business. You can automate your accounting, see real time reports, and communicate well with your tenants. Spreadsheets are too much trouble. You deserve better.