Would love to swap our knowledge in return, we've been researching for a bit.We also have another post over here about SKIP TRACERS: https://www.biggerpockets.com/forums/12/topics/1158109-skip-...Thanks!

I meet all the criteria for material participation and average stay under 7 days so I would be looking at a nice tax deduction against my W2 income.

I know this is an old thread that got revived, but I want to make sure that anyone reading this gets a view point from a local investor.Out of state investors must be very, very careful no matter where they are investing, but they also have to be very careful not to get ahead of themselves, especially as it relates to knowledge of an out of state market.  

4K sounds low for rent for that house, especially for 4 single people who may not be staying for that long.

I've only been investing since late 2020 in midwest markets (Detroit and Memphis), but I would be happy to connect and knowledge share if you are interested.

They will likely be better behaved and take better care of the unit if they know.If its a MF and I'm in a different unit, I can see the benefit of being anonymous, but even then unless you are a total "hands off" LL and let a PM handle everything, then its hard to stay "hidden"

What software is good for staying on top of due dates for everything else?

If you are subject to the MA "Millionaires" tax there is some (minor) planning that can be done, but nothing that requires significant knowledge to do it.  

I've been staying at ABB property's since they started.

That being said some of the areas do drop down a lot during the winter just due to lack of services running, restaurants closing for the seasons, and lack of events going on; so staying in areas near the year round attractions will be very important.