You must maintain the walking surface of your exterior steps and/or deck so as to minimize injury from slips, trips and falls by you or others due to weather or other conditions.

Streets in front of property should be handled by HOA, and then on your driveway and walkways/decks it is wise to hire a service or a neighbor that can do this on demand when snowfall happens.

The squatter(s) found a point of obscured vulnerability under a deck (an old boarded-up basement window) and exploited it. 

.$100k+......assuming you are talking MEP, deck, flat roof, etc. if you are digging out a basement consider another $80k

@ Derek Blades, Craigslist is not a good place to advertise your STR. 

Besides just cleaning between guests, we have a once-a-month deep clean that covers air filters, baseboards, ceiling fan blades, etc.

I do see a lot of rentals on the market with electric heat though.The boiler is unfortunately in a tiny crawlspace with access via removing a part of the deck hence PITA :-) If I don't have to ever do anything down there great, so trying to 100% solve the don't have to do anything down there problem which would mean get rid of the boiler and figure out something new.

There are many miscellaneous types of repairs that come up over time, and a handyman is a great person to have on deck to be able to call/text as a primary line of defense.2.) 💧 Plumber: A plumber is another absolute necessity to have as a go-to.

Maybe some additional info: my current plan is to redo the deck and kitchen in my current house, rent it out, buy the property, split the lot, build two houses rent one and live in the other, along with if I can put each under an LLC in some way.

At this property the dues include water, waste, outside maintenance (lawn, roof, paint, stucco, deck, gutters, snow removal etc).