We contract out snow removal and maintenance issues.

Are the tenants in charge of lawn/snow? 

I'm totally baffled why people are snowed into thinking they're"classic" when in the current form (pillowed 3x6) they're been trending for less than 20 years, replacing the standard 4x4s that were in for 60 years before that. 

No state income tax leaves you with Wyoming.Washington.Texas.South Dakota.Nevada.Florida.Alaska.subtract SD and AK for snow/freezing tempsSubtract Florida for hurricanes and high insuranceSubtract Texas for high property taxes and some areas with bad foundations/soil conditionsyou could say that also leaves Washington and Wyoming but I’m subtracting them for weather and other personal reasons. 

Update:  Court was cancelled due to a snow storm in January and then I left tbe country for a month.  

Then, the rehab cost was 78K where I used 53K from the rehab loan money plus 25K from my pocket. and now for the refinancing I got a loan for 217.5 K (which is the 75% of the appraisal value *I looked everywhere to get an 80% but no luck there*) and checking on the document I actually paid 8K on that closing.3) the property is rented for 1.7K tenants pay all the services + lawn care + snow removal4) My monthly payments that include PITI is $1,139. and that is for the refinance mortgage which is a 30y fixed at %3.625***on side note this numbers are rounded up to make easier the math and so I can understand better :)thank you for helping me

Are the tenants going to cut grass / shovel snow, or will you need to hire someone?

In addition to spending tourist dollars, I pay folks to mow lawns, clean yards, clean up the houses on turnover, shovel snow off sidewalks, paint, replace flooring, etc.  

I think its possibly causing some leak when it snows or rains, you can see the wood filler coming out in the second pic with some paint peeling off, appreciate if you can let me know how to address this gap along with the wood filler.

Do you have snow removal?