***EVEN IF YOU CASHFLOW IN REAL LIFE***Ready for the boatload of cherries on top?

And since I would like to go back to it being a STR when some of my life calms down in a year or 2, it doesn't make tons of sense to get rid of it all and then start again!

Charge more to traveling health professionals.  

A reserve is unnecessary, but I still keep around $15,000 - $20,000 in my account.The point is, that you should sit down and assess your finances to determine what the worst-case scenario may look like, how much you would need to cover it without impacting your life, and whether you will need to build a reserve.

To set the scene: A cost seg study breaks your property into two important categories:1250 "real" property aka the building, foundation and other long life assets.1245 property aka anything that can be accelerated such as 5, 7, or 15 year property like carpets, cabinets, or other site improvements.

He has lived here his entire life, and knows the area very well, and he is a general contractor and has been remodeling homes in our area for 20 years.

Quote from @Jerem Kaawaloa: I have spent the past 20 years working in health care and have only ever purchased properties for my own use, including a home and office.

For example, a buyer putting 20% down on a $500k home would pay around $500k in interest over the 30-year life of a typical mortgage at a rate around 6.5%.

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. 

Instead, investing should be a means to taking care of our needs and improving our life style.