The American small business landscape is strewn with carcasses of dead and dying small businesses that were started by people who did not plan before moving forward. 

Paint, landscape, driveway, walkway, patio need inspected and attention.  

But I would put money into the operating account and then let the LLC use that money as opposed to you writing any personal checks to the landscaper or the plumber.

How is the real estate landscape in Cook County changing?

No shanty fixtures, poor landscapes, dead environments, dripping roofs, overgrown beds.

CapEx (annual) 10.00% $90 $1,074 Gross Rent Multiplier   2.79         HOA (annual) $0 $0 NOI   $2,784         Utilities (annual) $0 $0 Cash Flow annual   $2,784         Landscaping/snow (monthly) $0 $0 Cash Flow monthly   $232         Other 1 (annual) $300 $0 Cap Rate   9%         Other 2 (monthly) $0 $0 CoC   5%         Total Operating Expenses $874 $6,882

Just looking at the numbers, given that you would occupy at least one building, the numbers that you could impact (reduce) in order to improve your personal situation would be the landscaping and property management costs.  

You're getting something for them (water, landscaping, insurance), which you'd also pay out of pocket for at another property.I don't know your market, but if you're seeing a ton of appreciation it may be worth holding onto the condo.

I just got a call and a picture from a tenant that a tree branch fell on the roof, part of the branch is still loosely attached to the main trunk of the tree.The branch itself is the size of a small tree with the diameter of the branch around 15" or so.I am heading up to take a look now, but wanted to post this as I figure my options.Can I get a landscape company to come remove the branch immediately or do I need to get the insurance company out first?

Floors throughout, kitchen, both bathrooms, baseboards, landscaping.