Lastly, after you receive advice from other Chicago area SLH operators & the local municipal agencies that will not only save you time but direct you towards ways to save you money, you are going to likely want to register your business as an LLC with the state and obtain the proper small business renters Insurance policy under your LLC’s name (if its just a 2-3br operation the policy monthly premium  cost will be very low and will shield you as an individual from the very probable situation of being personally liable for the behaviors, damages, & actions of a traditionally high-risk short-term tenant group bc no landlord’s homeowners insurance policy will cover any damages or personal liabilities that will occur when they discover the nature of the operation.

I am drawn to the idea of minimizing my housing expenses through house hacking and understand multifamily homes such as duplexes and triplexes are difficult to come by in Portland proper.

If you have a PM, he should have properly check out the tenant prior to renting.

Outside of Houston Proper (where a lot of the multifamily is overpriced, in an awful area, or both), finding cash-flowing multifamily rentals can feel like a sisyphean task.

It might be a good idea to have your lease forbid blocking windows with foil, or other opaque items other than curtains or commercially available window blinds (that are not flags or political).Drug dealers, and fake drug dealers tend to block windows so no light can get in, and no Police Officers can see in.As far as flags it's not a proper venue for National flags, and gives you leverage in case someone decides to hang flags offensive to some (such as public display of WWII Axis flags, or socio/political flags) that might be detrimental to your rental business.Good Luck!

But make sure that you have the proper finish out.

House properly 4.

To avail yourself of these systems you need the proper legal apparatus and software system(s). 

Had to drive 14 hours on day of closing to get proper documents to all parties.

Had to drive 14 hours on day of closing to get proper documents to all parties.