Starting a PM Company, Need Advice

[Bradley Chiakas]

I created a real estate LLC a few years back. I am financially independent (still creating wealth and living purely with passive income). I am managing 6 properties currently, 4 of my own. 4 in Playa Del Carmen, Mexico, and 2 in Houston.

It has been a dream of mine for a while to move back to Chicago where I grew up. I now have some experience managing property, an LLC, company logo, and soon a website. I have a few questions about starting up a property management company. My ultimate goal is to create 8-10k worth of income and provide work for a couple of close family friends that are soon to graduate school.

My plan is to create the website, google ad words, rent a place in Chicago and get an owner base underneath me.  I'd like to have two rental markets with a couple employees in each and have the flexibility to work from either. I will also be advertising property management services in Playa through said website. 

I know this is a massive undertaking and I have a ton of work in front of me.  My wife has volunteered to stay in Playa while I do this to ensure the quality of our vacation rental service business does not suffer while I startup in Chicago. 

Before I do anything of the above, I am putting together a business plan.  And I would appreciate general advice from experienced PM professionals and also have the following questions:

1. How should I structure compensation for interested parties?  I listened to Podcast 30 something and heard a commission based structure based on each unit rented out.  Anyone know how that would work?  For example, say we screen and place a tenant in a condo that rents for $3k/month and 1 month cost to place a tenant. How much commission would said employee get?

2. Are there any regulations of certifications that need to be taken to be legal?  Does the company need insurance?  I don't foresee growing past maybe 80 or 90 properties, as I still value time.

3. How long does it typically take to get to 5 owners, 10, 20+? I plan on attending every real estate meetup I can, marketing online, and doing everything possible to grow. Any advice on how to increase the rate of meeting owners?

4. What sets my wife and I apart is that we are able to maximize operating efficiency and income with short term rental properties.  While I manage 1 long term rental. My "wheelhouse"  is in short term rentals.  We are able to remotely run a 3 bedroom town home in Houston, with little stress. That of course largely depends on the team we have helping us with maintenance, cleaning, laundry, etc. Do I market both short term, and long term rental services? It's a little more difficult although possible in Playa Del Carmen to remotely manage. 

Thank you for your expertise all!