It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

My recommendation to serious real estate investors is buy an opportunity in any segment, do the math (it's all about the ROI; some investors fall for the 'commercial' is more prestigious chest thump to find that losing money isn't very prestigious at all), and plan on proactively running a business. 

Leverage technology early and put everything in the cloud, so you can access info wherever you are.Make sure to get properly licensed and obtain E&O Insurance.

., HVAC tune-up, plumbing fixes)Deep clean entire property pre-listingEstimated Cost: $5,000Total Estimated Renovation Cost: $145,000Project TimelineWeek 1-2: Planning and DemolitionFinalize design and materialsObtain necessary permitsBegin demolition (kitchen, bathrooms, floors)Week 3-5: Structural and Major InstallationsInstall new cabinets and countertops in kitchenComplete bathroom tiling and vanity installationRefinish or replace flooringWeek 6-7: Painting and FixturesPaint interior and exteriorInstall lighting, hardware, and plumbing fixturesWeek 8: Finishing TouchesLandscaping and curb appeal updatesDeep cleaning and stagingTotal Timeline: 8 Weeks*This link comes directly from our calculators, based on information input by the member who posted.

Great people to work with and I plan on investing more with them next year when I sell another property.

The email was short and challenged us by implying we were looking for investing planning and not tax planning.

We plan to build a cabin or cabins for our family use and an STR.

When i press on the cracked areas, it does not appear soft or wet.I plan to fix it, but I worry it may reappear in months.

The mortgage was also raised due to insurance issues to about $1,950… so I am not making much cash flow, more like a cash trickle.

Bigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.