let me break it down.1-4 units: this falls under traditional "residential" financing, that you may already be familiar with from single-family.

I think your expenses are too low, and if you adjust properly, its likely to be close to break even for you. 

I am also wondering if there are any tax breaks for something like this though. 

The gel coat has to be regularly refinished and fat people can actually break it. 

Hello folks,We recently bought our first duplex and we are obviously house hacking.A small problem though, we have an outdoor staircase which is very unstable and ready to break off anytime someone is on it.Question: how to fix this problem ?

Lets be real, if you're M-Day (which it sounds you are) you'll only be obligated "1 weekend a month" that really breaks down to "I cant work 2 days a month" which realistically, isn't going to make or break you in any occupation (unless its a weekend only job.) 

Break down the returns you have earned from your current properties and be able to talk about them/increase them over the years.

You cannot make money in D-class unless you break the law.

Unfortunately, the areas I am looking at are in very high demand (River North, West Loop, Fulton Market), and have prices such that I would at best barely break even with rent after taking into account HOA and taxes ($300k-500k range for 1-2 bd, HOA in the ~$500/mo).

Thanks to my high W2 income and not having any debt, it would also be easy to get approved for some cheap 2.x% financing.Having never owned real estate, a good way to get started would be by owning my primary residence for a while, with the intent of eventually renting it out in a few years and in the meantime seeing how I feel about maintenance and home ownership in general.Unfortunately, the areas I am looking at are in very high demand (River North, West Loop, Fulton Market), and have prices such that I would at best barely break even with rent after taking into account HOA and taxes ($300k-500k range for 1-2 bd, HOA in the ~$500/mo).I understand condos in downtown are generally a bad investment, but I really don’t want my quality of life to suffer by moving far just for the sake of home ownership.