I look forward to any advice on how to make this transaction as smooth and tax-free as possible...Thank you!

Currently, I'm engaged in house hacking on the west side of Chicago, and things are going smoothly.

Take the amount of work you think it takes to get a property running, then double it, then double that energy again if you want to make it run smooth and efficient Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Full doc is a must because we can't afford any surprises once in escrow/under contract, and on the plus side allows for a quick and smooth closing. 

CACU- bought investment prop w them and had smooth, quick closing!

I bought my first condo earlier this year, and it's been smooth sailing so far. 

It's a smooth and easy process. 

Investors in these markets can keep riding the wave, and as long as everything runs smoothly there will be no issues, but once an “unforeseen” event occurs, the risk becomes apparent and market participants reprice the asset with that risk fully baked in, which means loses (substantial) for previous buyers.

I just make sure the rehab goes as smooth as possible ..stay on budget and time..  

Setting aside some money up front and also each month will smooth these expenses out.