I later had a tenant allow a homeless guy to stay and put some stuff in his place and he brought in bedbugs.

I would have to let a friend go homeless before I rented to him, just saying.

Loitering and stolen license plates happen in every neighborhood... but assault with a deadly weapon, shooting on an occupied dwelling, etc. only happen in the worst neighborhoods.BUT -- also take into consideration that this property is located directly next to a main street - Madison Ave - and main streets almost always have more crime than residential streets because there is more foot traffic, more loitering, more homeless, more stores, parking lots, etc. where lots of crime happens.Ultimately, you want to see the property in person and drive the neighborhood, but if you can't do a "virtual driveby" on Google Maps and that will help you at least get a feel for the area.

Yea, my risk tolerance isn't super low, but I don't want to stretch myself too thin and end up a "successful to homeless" story either if something should happen. 

Owning a primary residence keeps you from being homeless and from taking less desirable jobs because of need to pay bills. 5.

There are immaculate neighborhoods that are a block or two from large homeless camps.  

And In Milwaukee there are (Homeless people) who have no idea how to buy a house.Maybe some of you Milwaukee-ans could spend (zero dollars) and then rent a trailer, pick up a local homeless and drop him and his meager belongings off at his own new house.

You would be willing to live in a rougher neighborhood for a short period of time, because it is better than being homeless.

Getting evicted is almost never a reason to be involved with CPS, as almost nowhere in the US is being homeless with children considered a danger to the child in and of itself.

I think tiny / shipping container homes could be a good idea for housing homeless veterans or to use for sober housing.I'd guess that if you got the right support groups behind you, that could grease the skids for both financial backing and help getting regulatory roadblocks cleared.