In a lot of places, evictions are quick enough it shouldn't be an issue but I do tend to live by the motto "never underestimate how much damage a pissed off tenant can cause in just a few hours."

Financially it only makes sense to invest remote if you have a sufficiently large economic delta between the market you live/work and Milwaukee.

I work in group home settings for a living and at my previous facility there were two clients per bedroom which would give you potentially 8 in your house while at my current job there is one client per bedroom which would only be 4 clients in your home.

I live in MA and I know it is a nightmare to deal with tenant here.

Will be difficult because you currently live in the property . is the 2nd unit livable and just looking to renovate ? 

Good to know as I have a property coming on the market and we had one off market offer already all cash but at 10% list price discount (which we most likely will reject).Curious if you think the california fires will assist the market since many of those people need places to live for years and I am guessing some will flee california?

I've been living in my current house hack for ~1.5, and I placed my tenants in September 2023 (lease is up at the end of August).

Quote from @Vince Scipione: Yes, they are a popular choice where I live and work, however with the ever fluctuating cost of oil heat, many people have swapped over their boilers/furnaces to what is called a "Propane Gun" essentially it is a device that is affixed to the front of the furnace/boiler that injects the propane and ignites it.

I have lived in GA all my life 49 years so far.

I'd recommend working with a good strong property manager that lives in that area that can check on them.