@Brett Riemensniderwe don't know all the details, but as i said that's a very expensive way to buy property - if you can't afford a property without overleveraging then you might just have to save up more.

Best of luck to you.

I really wanted to convert the residence to a rental property, but everything I have heard about doing so in Cook County has been very concerning.

Very helpful.

One of the very few times I heard a financial advisor provide good advice.

Best time to plant a tree was twenty years ago, second best time is today" You are not too late to get into the REI world!

Quote from @Brendan Jones: When it's a home you intend to live in, I lean towards focusing on what you want, then making it work as best you can as a short-term rental.

Became very unresponsive very quickly, did not complete agreed upon work, made false claims about capacity and what they would do, etc.

It's not the best setup nor the best part of town, but you can make it work.

Sometimes the best investment is found in a 'transitioning' market that is just outside the 'great' market and is in play to be the next great one.