Small, incremental steps practiced consistently take us much further than occasional bolts of motivation.While motivation gets us revved up, discipline provides the staying power.

I would avoid dsl at all costs. yes weather can play a role but for occasional bad weaether id take a hard look at starlink. 

I wouldn't call it a 'rough' area (not a lot of crime) but all dwellings are 60-100 years old with the occasional run down property on each block.

You have an occasional listing the surrounding counties, from Brookfield, to Cedarburg, etc but that is not really the question.

But if you live far away from your STR / Airbnb / VRBO property, how do you deal with practicalities like occasionally replacing furniture?

We occasionally have problems with this in our SFRs.

So if you are willing to invest a fair amount of money in something to just have it pay for your free vacations occasionally, you have a safe bet, but if your goal is to make money, self management would be the most secure way to go, if one or both of you is willing to learn how to promote your cabin on social media, rental platforms, etc. 

I'm looking for someone who can send me SFR and Multifamily home listings as well as be able to show properties on the occasional weekend.I look forward to hearing form you.Thank you!

I occasionally browse redfin or realtor.com for areas that I dont have access to the MLS.

So aside from occasional repairs and exterior cleaning demanded by the HOA I have had to put in about 4k.