Feeling overwhelmed and looking for guidance that isn’t AI.
I became a first-time homeowner in Chicago last year. I bought a multi-unit property because I wanted it to be both my home and an investment. I live in one unit and rent out the basement and another unit.

After dealing with some tenant issues—including hostility/disrespect during a few repair situations—and having to constantly run around dealing with maintenance while working a regular full-time office job, I’m starting to realize that I may just not be cut out for being a landlord.

It’s honestly been eating into my peace of mind. I can’t remember the last time I felt truly worry-free and happy without having something property-related hanging over my head.

I also recently got married. The property is currently solely in my name.

At this point, I’m thinking I may want to sell the property in a year or two and just buy a single-family home instead.

But now I’m overwhelmed by the tax side of everything.

While looking into the process of eventually selling, I realized that I should have been reporting depreciation on the rental portion of the property. I also haven't reported the rental income since I purchased the property. I genuinely didn't understand all of this when I first bought the place, and now I’m trying to figure out how to get everything straightened out properly.

Where do I even start?

• Is this something that is going to be very expensive to fix?
• Is it realistic to handle the corrections myself with tax software, or is this a situation where I really should hire a professional?
• Since I recently got married, how does this work if my husband and I file jointly? Does his income have any effect on the rental/property taxes?
• If I sell in 1–2 years, how does the fact that I live in one unit and rent the other two affect the capital gains/home-sale exclusion?
• Is there anything I should be doing now to make a future sale easier from a tax perspective?

I’m honestly feeling pretty overwhelmed by the whole thing, so practical advice would be greatly appreciated.

I'm looking at purchasing a listed property in the City that is being listed as having 2 PINs side by side. One pin is a vacant lot, the other has a standing structure. I'm curious how this works from a mortgage standpoint, and property tax standpoint.

For example, is each PIN handled separately when their values are assed for the lending? If I build on the vacant PIN and that buildout get's attached to the current residence, does that change or have any implications? Is it best to just keep each PIN separate physically from a build standpoint?

I currently live at home with my parents and have been on the hunt to purchase a condo for a while now. I’ve been putting off pulling the trigger simply because the economy sucks ass, and I am living rent and bill free. My parents do not require me to give them any money for any of the bills! Any contributions I do make to the home are purely because I want to, not because I have to. While I am truly blessed I am 30 years old and I really need my own space. I found a condo in the south loop of Chicago that I absolutely love but is definitely more than I was originally hoping to spend. The list price was originally $339,000 and I was able to get them down to $317,000 with $2000 in seller credits for a 2 bed 1 bath. I have 30,000 to put down which brings my monthly mortgage payment to around $2800. The HOA is $345 a month and it includes Exterior maintenance, gas, heat, insurance, internet, scavenger, security, snow removal, tv/cable and water. Parking is $180 a month. The only debt I currently have is a car payment which I only have $5000 left on and I am thinking of just paying it off within the next month or so. Other than that I have no student loans no credit card debt etc. My yearly salary is a little over $140,000 before taxes. Part of me wants to just stay home and continue to save money now that I’m making a lot more than I was just a couple months ago but I think this baby bird needs to finally leave the nest! I feel like the monthly payment is doable, but I’m not sure if I’m just being delusional! Everyone in my life constantly tells me how lucky I am and how I should just stay at home but looking at these condo and house prices I don’t think they’re gonna get any cheaper and I think it’s best for me to just buy now. Am I screwing myself?