As I mentioned, advanced tax planning opportunities are going to be limited so finding a highly specialized CPA is probably unnecessary and going to reduce your pool of otherwise qualified accountants.

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

Hey Jason, As myself and other tax professionals have mentioned it's considered "in service" once ready and available for rent-and at that point is when you can start reporting it, you can begin depreciating it etc. 

They are worth the money for a good hot tub that is mentioned all the time in reviews and doesn't have a ton of issues.

If you are using an agent, they should be guiding you on this.Aside from that, there's a few things:You mentioned this is a house hack and your first one.

I am actively looking to connect with investors interested in [mention specific types of investment opportunities,  single-family homes, multi-unit properties, distressed to expand my portfolio and deliver strong returns.

What the concept you mentioned is talking about is leveraging equity to gain cash vs. selling essentially. 

If they do, your best bet is a local community bank that funds these types of properties.Another option is a private lender but that money will be pretty expensive, as mentioned 10%  + 

I am now shopping to replace, but curious where I can learn more about the pros and cons regarding a policy like the one mentioned.  

these rulings over the last 10 years have eliminated much of the angst seen around the "hold for investment" issue mentioned above.