Maintenance procedures such as snow and ice removal, steps and hand railing, etc. 

Installing small things like a heat pump and insulation with new double or triple-pane windows for snow regions.

Also have you considered any additional weight of snow on that might accumulate on the lattice and the rafters?

Our current rental was purchased for roughly $340k 7 years ago and is worth in the mid $500’s now and is paid off, and our primary was purchased for $430k 4 years ago and valued low to mid $600s and we owe $180k.Option1 we are considering are a fix and flip to provide cash for a down payment for a long term rental to allow the rent to cover the mortgage and at least break even.

The good news is that my wife and I are going to move into our in-laws home In Alaska because the snow bird in Arizona, it’s a great opportunity for us as we can now rent out our 5 bedroom 2 bathroom home in anchorage.

Most lenders on BPs are investor friendly and won't hound you with incessant follow up. 

As a hard money lender who works with many investors in the Portland area, I can share some insights on maintenance costs for multifamily properties in this market, though individual experiences may vary:Lots of investors report a slight decrease in maintenance costs during winter months, bc of:- Fewer landscaping needs - Less wear and tear on HVAC systems (as heating is generally less intensive than summer cooling)- Reduced tenant turnover in winterWinter-specific issues can arise:- Potential roof repairs due to heavy rain or occasional snow- Gutter cleaning and maintenance to prevent water damage- Heating system repairs or maintenancePortland-specific factors:- The mild climate helps reduce extreme weather-related maintenance issues. - Older housing stock in some areas may require more upkeep. - Strict local regulations can also sometimes increase compliance-related maintenance costsCost-saving strategies I've seen help:- Preventative maintenance programs can help reduce overall costs obviously - Some investors report success with in-house maintenance teams for larger portfolios- Energy-efficient upgrades can help reduce utility costs in the long runYour specific costs will depend on factors like the age and condition of your properties, your management style, and the specific neighborhoods you're invested in, but hope this helps!

So I dress & head over to discover she had our maintenance guy on the lower roof trying to remove the melting snow & ice.The ambient thaw had started & the elderly lady decided to open the window several hours earlier.....she doesn't pay for heat..YET!!!

If you go forward, make sure they handle all maintenance & repairs on the property too because these organizations typically have in-house staff..Snaking toilets, repairs, grass cut, snow removal, paint...Make sure you're covered with insurance as well. 

STR in those areas do well year round because of fall colors and ski resorts and snow mobiling if they are on a lake, but on the flip side you are paying significant more because they serve dual purpose.