If this is your goal to live off of rental income you will need to acquire many properties until you reach your overall goal of making enough off rents that will cover all of your living expenses plus a little extra for fun stuff.

I bought our current house in the middle of a harsh winter because we were relocating and need to find a place. 

Obviously, some markets are about to get hot in fall and winter, may not make sense for them to discount. 

Someone will buy that, and then have the pleasure of mowing or more fun-weed eating that to keep the city off your back.Not sure about SD, but I tell everyone you need time and money

I’m really early into the research phase but would be prepared to “pull the trigger” over the winter (eg purchasing a property to setup the tents) but ran into a bit of a “wall”.I’m pretty close to Blue Ridge and love the area so have considered a STR there for a while.  

You want to bank reserves there to see the future cap ex because if you don't, you get another property and then two furnaces go out in the winter at each and you need 20k and now they both cashflow nothing.Your asset will appreciate and you can value add to rent add by making smart decisions on upgrading tenants.

We mainly use it for laundry but don’t use it much otherwise.I wonder possibilities of doing STR for winter since I live very close to ski resorts.

Keeping their taxable income down is a huge advantage for you as paying that from the sale would not be the most fun, although maybe I am incorrect since the property was inherited. 

Not fun!!

When bought my rogers park 4 it cashflowed about $12k annually now with rent increases and one unit as airbnb I net out on tax return $40,000 off one property, sure the equity gain is higher but cashflow makes life more fun.