With the summers off, I am looking at a seasonal business for some extra income.There is an ice cream shop that I am looking at.

Also, empower tenants with a bucket (some brands come in boxes) of ice melt, one at each door (few will shovel, but most will throw ice melt on their porch between your shoveling intervals)..Whatever you do (DIY or contractor), have a plan in place and reasonable maintenance intervals (like biweekly mowing, or shoveling with 2'' or more, inspecting for ice etc) and don't just rely on the kindness of strangers (or tenants) to do it.

I believe the bulk of the dues go towards insurance, making the whole thing a form of self-licking ice cream cone.I would like to dissolve the HOA. 

How are those ice dams coming along?  

I was reviewing and see that in the last 3 or so years, the  calls I've gotten from tenants are 60 % related to appliances....example, Ice maker is not working, fridge is leaking. 

If this were a game of hockey, my advice and analysis could be based on the premise of telling people to invest where the puck is going, not where there puck is.And the picture I'm "painting" is more so a collage of newspaper articles and reliable sources based on facts.

>> Icing on the Cake of Negligence:Who in their right mind, would upon SEEING a house ( DISCOVERY) just shut the door and leave, and drive 30 minutes back to their office with a water heater streaming full blast with 20 ft plume in the air hitting the ceiling and seeing drywall collapsing and walls covered in black moldNOT CALL IMMEDIATELY FOR HELP!!!

In addition, it’s easy not to remember exactly where a roof vent or sky light is underneath the snow and ice.

typically shingles will run you $20/bundle (3 per 100 sq ft or 1 Square) for lower end, install depends much on tear off and prep or shingle over and prep, we have opted for Steel when ever reasonable to do so, it costs about 10-20% more up front, but will out last me, and does not have Ice damming problems we see with regular shingles in the north. standard shingles, you can expect about 1/2-2/3 the stated warranty actual life span, so 40 year shingles will last about 20 years, but steel, even 40 year has been known to far exceed the 40 year warranty, I can typically get a roof done in steel with a 2 layer tear off, and steel installed for around $4-6K for a 13 Sq roof thats material, labor and disposal, I just has a 11 sq one does with dimensional shingles (steel wasnt practical) for $2,700 including tear off and disposal. keep in mind, the cheap guy may not be the best value, there are a lot of hacks out there, and anyone with a pitch fork, a hammer and a nail gun calls them self a roofer. 

For example, you have a snow removal company remove ice and snow from your properties parking lot at 7 am the day after the storm but if someone slips and breaks their neck at 6 am they would have a legitimate claim.