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

The house is currently under management so I’d think they’d take care of getting top market rent but I think we all know that management companies can be hit or miss.

If you can find a fixer at a good price, with room for an ADU, and the comps are good, then you have a deal.Are you planning on flipping or long-term holds?

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

You will also provide the whole amount if you plan on repaying the loan in full beforehand.  

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

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.

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

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.

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