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.

I would like some advice on how to get a start and what a good approach is with barely any money.

If the property is in rentable, but barely, condition currently, you will likely have higher turnover costs.  

.$10,000 can barely cover the cost of a $100,000 real estate purchase assuming 3.5% down and another $6,500 that goes towards closing costs and 6 months of reserve that the bank will require.I would consider saving up another $10,000 before considering a real estate purchase, atleast this way you would have more playing room with what you can buy and having more contingency funds.

@Mason Hickman I'm hoping the other neighbors aren't too annoyed since the next door neighbor is a outdoor hoarder with barely any grass visible, which should distract from my tenant's yard being overgrown.

However, although fall is super busy in this area, we are barely booked, but our competition with smaller properties are booked solid.

A fourplex has barely more work and should cash flow at least as much per unit.

In CA any legal mapped parcel can (baring a few exceptions) always be segregated later without another subdivision action unless it is remapped as a single lot.

How much bare usable ground is there?

No Pink Trailers that wipe out your value.