Right after I closed on that one the insurance company demanded I make a couple thousand dollars of repairs.

looking to make an offer

You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

I do pretty decent for my age, and I live at home still, so I've been saving up a lot of money.

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

The money that you end up owing to repay the loan over the 5 year term is now post income tax money unlike how you traditionally are supplying your 401k with pre-tax money.  

Check with your broker and make sure this fits with your local laws.

So you'll need to bring your own money to do that.

But unless you get a value-add property, purchasing real estate really doesn't make much sense in this environment?

Make sure you setup your Goals correctly so you are measuring things like phone calls, contact forms, tours scheduled etc., 2.