But the good news is, you don’t need to have all the answers right away.

That property looks fantastic actually, I think sorting out the budget would be our biggest challenge.

If you do not have something kind or helpful to say please refrain from saying anything at all. 

I moved many times during my Navy career to markets all over the US and even Toronto.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

I also have a list of all the other local meetups that I'd be happy to share...The super power I've found over the last 5 years or so investing is FOCUS!  

I would not start paying off properties (if at all) until you are done buying as it will slow you way down. 

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

With a dynamic real estate market, diverse neighborhoods, and high rental demand, Chicago is a fantastic place to invest in house hacking. 

Roof lines, window styles, and masonry/siding all play into this natural flow, and the biggest mistake you can make when designing your flips is not following the flow that is already present!