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.

If you or anyone have a good resource or calculator on this, I would greatly appreciate it (hope I didn't break any rules with that statement)  In the past written off all of the HELOC interest, but that was typically what I had used for upgrades and repairs on my primary residence.

If you follow this link this is a really good article by HGTV that breaks down further the costs/benefits of a pool and if you should keep it or not.

@Justin Sawyer BiggerPockets has a book in their bookstore that is strictly on that subject, and I think it breaks it down by state. 

Your boots on the ground will be most important in understanding the neighborhoods and checking if the areas are well kept or not--especially since Indy is well known as being very street by street.We have had some attempted break ins in our vacant units, but this can be mitigated by getting appliances towards the end of the rehab and not putting them by windows, boarding up/covering windows, and getting a security system like simplisafe.

Of course I know nothing of the condition, but you only have up to $40k/deal of renovation budget to break even.  

As an hvac contractor, this is very simple.You buy it, you warranty it when it breaks.I buy it, i warranty it when it breaks.

Your goal is to get a qualified body in the unit ASAP paying you so you don't have to pay out of pocket.