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Imagine making millions of dollars over the course of your career and then having to pay 30-50% every year to uncle sam instead of compounding that cash over time.This is exactly what real estate professionals have learned to mitigate.To reduce their taxable income, they just buy a building every year, do a cost seg, and use depreciation to reduce their tax liability dramatically.Their personal wealth snowball grows much larger and much faster than their W2 counterparts who give most of their money back to the government each year.Following this strategy as a real estate professional is one of best ways to end up with a much larger net worth at the end of your career.

Tax deductions / write-offs should be a second concern.There are some rules that you need to follow to treat a short-term rental as 'active'(non passive) income which would allow you to offset it against other forms of income such as rental income / wages.

I’ll be splitting the rent 50/50.

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. 

Looking for something with low acquisition cost, and meets or exceeds the 1% rule.  

It could be 50% high, 50% low or right on the money but no matter which of those three it is makes no difference.

In Winnipeg it's at least 50% more.

For items not available before the SoE and hitting the market after the SoE, you can raise prices a max of 50%.

Owner occuppied loans regualted in every state .. must have state license and NMLS registration.NON owner occ loans on 1 to 4 units are regulated same way in about 15 statesin the other states they are unregulated.Keep in mind though investor loans do not follow the same rules as owner occ and rates can change charges can change closing dates can be blown through etc