Personally (as a STR-focused REALTOR), I would never give you numbers and tell you you can hit them. 

Also, you don’t need a business license just to look at properties, but if you buy a bigger property, like a multi-family unit, you might need a certificate of occupancy, depending on the local rules.For business trips, most expenses can be deductible, but if it’s part personal and part business, you can only deduct the business portion.

Do you have a 501c3 that you operate under (and rent the house from yourself), or do you purchase homes with an LLC or personal name, and run as a regular business? 

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

However, I think for the average person this is probably not true. 

Here is my favorite (among several others, just as hysterical) part of this case:"...Petitioner’s testimony that neither he nor his son used his personal bedroom,living room, or kitchen for personal reasons strains credibility.

Continue to scale my personal RE investments and learn!

If you do decide to do mailer(s), then I would advise you to personalize the card and do a handwritten note. 

We take a "whole person" approach.

@David To In Texas there is a way of using tenant personal property to pay past rent.