I've done and been a part of many Chicago zoning changes...they take a very long time and a lot of upfront money...unless you are planning to add multiple units and do a full renovation, the ROI is probably not there.

Hopefully, the tenant takes the hint after today’s conversation, but if not, you’ve got a solid plan.

However, the fact that your tenant intends to pay $800 through the app while their rent is $1,200 raises questions, it’s worth clarifying whether they plan to pay the remaining $400 separately and how that affects both of you.Before signing up, consider reviewing the app’s terms, checking online reviews, and confirming how quickly payments are processed to your account.

With patience and a solid plan, you’ll be on your way to building a successful portfolio.Good luck!

The IRS doesn't care which of you is on title.

Unless you have a solid plan to turn this around, selling now and cutting your losses might be the best move.

Over the next couple of years, I don’t plan to use the property often, but I may stay there occasionally when it’s not occupied.

I have 2 properties i'm planning to purchase and wonder how is the crime and rental market in there. your response is much appreciated

The GC is a business person who doesn't care about your ARV, LTV, or your budget.

You need to make a written plan with him to get this over the finish line, with cost estimates.