We both have some home repair skills, but would likely need to hire out larger work such as electrical, plumbing, roofing, siding, etc.Thanks for the help!

When you get tenants paying low rent on month-to-month deals, you face choices.

I might recommend one GC for a larger project and a different one for a smaller project.

Reason why I mention this is FHA has a guide line that requires the primary owner to live in the "Main" house or occupy the larger GLA.

Given your situation and concerns, here's a breakdown of considerations and advice:Pros of Renting Out Current Home and Buying a New Primary Home:Living Condition Upgrade: Moving to a larger, newer home with boutique features can improve your living space.Rental Market: West Town in Chicago generally has a strong rental market, which could provide good rental income from your current home.Portfolio Diversification: Adding another property to your real estate portfolio can enhance diversification and potentially increase long-term wealth through property appreciation and rental income.Cons and Concerns:Interest Rate: The current interest rate of 7% on a new mortgage is high, and there's uncertainty about future rate decreases.

It's their choice, as adults, to sell it for cash and off the market.

I'm saying be careful where you put it, because if you make the wrong choice you could lose your home due to not being able to pay the taxes, etc...e.

So why not advertise that their choice of grocery delivery, prepared meals, or fishing gear are included? 

I can understand why they made that choice, but it's tooough right now to look back. 

You don't say where you are, but for much of the country, larger sheetrock jobs run between $.80-1.10 per square foot of wall space -- that's labor and materials for hanging and finishing (ready for paint).