I am interested in having a long term investment, I may be breaking even or have a slight loss depending on the rent but I consider having an asset paid off a win.

So making sure, I nail it, I wanted to reach out to the community to see what data I should request to make sure I come up with my NOI  to properly calculate my CAP RATE...This to request:Income+Rent Roll +Leases  ( When under contract)+Tenant Estoppel Form (While under contract)Expenses(They sent me Profit andd Loss Statement) I asked for an expense report but they manage there on properties and Im questioning the expense report they sent.....

If you aren't keeping track of the carryforward losses you could be missing out on tax savings in the future. 

You're essentially taking a 10-20% loss on day one. 

Also, my current CPA (who also resides in Chicago) is great and also specializes in real estate.I will add that spending the necessary money on a solid CPA is worth its weight in gold and pulling the trigger before you feel like you can afford it is a good thing!

The longer you're in the business, the more weight you'll carry - but ONLY if you know what you're doing.

Also, to further protect yourself from large assessments, a condo owner can get what is called an HO6 or loss assessment coverage through their individual insurance carrier.  

We’ve all heard the terms fear of loss and fear of missing out.

I'll definitely get all of my investment and money spent on overhead back in the refi, but do I continue forward with the BRRRR, take the small loss each month, and bank on rates eventually coming down some more where I would refi again to bring the payment down OR pivot to flipping it where I'd make, easily, $40-50k net profit AFTER setting aside capital gain taxes?

The learning curve a killer but now I am stuck on unloading my burden selling it to break even or renting it out at loss.