I’ve heard a little bit about the legislation towards landlords in Seattle and how that’s been tricky for some folks.

We actually first learned about this legislation from a tenant bringing it up (whoops!).

Unless there was sweeping legislation passed in this state within the last few years that miraculously went unnoticed by me and others, that advice should still hold.I do not put "no section 8" in my ads, but I require first,last, security at signing so that self-selects all of those people out anyways. 

It's best to stay away from this, except where a path to both meeting code and legalization may exist (for example, California's ADU legislation under which unpermitted garage conversions, units permitted as rec rooms, unpermitted additions, etc can become legal residential units once building code and some limited zoning requirements are met).The tricky part is to understand when zoning and building codes interact, i.e. when required renovations to bring a property up to code trigger the loss of legal nonconforming status.

And if it turns out you've made a mistake on a tenant, the legislative headwinds make it very difficult to un-ring that bell and terminate that business relationship. 

If he doesn't a hire local property manager for Madison or Milwaukee it may be hard to keep up being across the country with the legislative changes, municipal codes, etc.  

Even so, if you aren't submitting any claims to CMS I wouldn't be concerned about legislation.

I would be very worried about the rent control legislation that keeps getting tossed around in your area as we have seen a flood of investors moving their holdings over here to Idaho because of just those things. 

PS: properties with ADUs or DADUs cash flow better than multis in Seattle, and given the city’s new legislation in 2019 these ADU investments are looking even better.