@Danny Day  Reverend @Lucas Carl was kind enough not to mention a tenant overdosing in your vacation property, people cooking meth in your vacation property, people breaking in to your vacant vacation property for a free vacation and a free HDTV, an unplanned fatality in your vacation property, etc. 

I was reading another thread on BP about the difficulty of evictions in Cook County which definitely worries me a little bit, but I guess that just means very stringent tenant screens are a must.

Yes, there is luck, but just saying, note investing isn't something you just wake up and do one day because you have a pot of money.

The dwelling unit is a non-housekeeping furnished room or a unit without cooking facilities; or5.

Ill use my business affiliations to sweeten the pot while creating business for them. 

Hey @jordan - In Illinois and specifically Chicago / cook county you never know what is going to happen with property taxes. 

google steve cook.

.)- Tenant operations that may be harder to insure (cooking, woodwork, manufacturing, etc.)- Construction of buildings/fire protection that may impact the insurance (frame construction in a non-hydranted area or one with distant fire depts)I echo the posts that emphasize the importance of an experienced real estate attorney. 

In addition Cook County has set up few new classification for properties that are converted to STRs. you can visit the assessors website to find oit more.

I will add a $5,000 loan to his pot.