A two-story in a good school district will have no problems leasing on a seasonal basis.

I am not an seasoned RE investor like you, I am just starting out.

There is a seasoning period needed for deposited funds.Lots of doubles available in Buffalo for an FHA house hack.

As for furnace, you can probably get better pricing if you do it in the slow season.

We have a strong 4 seasons in north Idaho and after 3 years it still looks the same.

Even as a relatively seasoned STR'er I've definitely learned some good stuff from his podcasts and I'm guessing his clients, who are often very new to STRs, learn a ton for their tuition.It definitely seems like a different kind of client he's targeting than we do here. 

I'll add that it's important to factor in the seasonal nature of STRs into your income / expenses.

I would be a 5th wheel stationed on a fixed lot at least for a season paying  monthly rent on that lot near the beach.

@Brandon I Garcia  not the best timing for such discussions in the heat of the tax season, sorry.However, if you read several weeks worth of posts on this forum, you will get the answer to your question.Also, where are you geographically?

@Marcus Gaethke the Dells are very seasonal, so one problem I see is high vacancy in the off months.