To ascertain the effect on your tax status, including any potential advantages and deductions, speak with a tax specialist.Consider how your condo purchase fits into your long-term real estate investment strategy.

There are strategies for folks with short-term rentals (7 days or less) that could work here potentially. 

Yes, there will be limitations of a TN financial institution as I live in CA, and I have read articles about potential tax and filling season issues if you bank outside the state where the business is registered. 

Afterall, the midwest states are known for their cashflow but also the potential for slower appreciation.

Hey @Andrew Singer - To be completely honest, I've found it hard to find a Chicago broker that I know, like, and trust, but importantly will keep working for me on a regular basis (quarterly minimum) to review and look for potential savings.I have a couple of good guys, but no one so far that is a grand slam. 

However, you could still have - cashflow on paper, but still break even or potentially have + cashflow on your taxes.

I have a line on a deal for a property that I believe is undervalued and has great future potential for improvement.  

I’m learning everything and anything I can by all available means, but would love to find someone in the same market who would possibly be willing to share their wisdom and potentially walk me through an actual transaction (simply as a spectator on my end, or in any capacity you’d allow me to be involved in).

My potential profit that would have been in the job was converted to equity.

If you are going to pay turbo tax rates, you will get turbo tax quality and potentially miss out on planning and strategy which is where the real value of a tax pro comes in IMHO