The people who struggle here usually underestimate those factors.One thing I do differently than most: I share actual performance data from my rentals—purchase prices, rehab details, rent numbers, lessons learned, and backstories.

James and his people who manage the program are nice and give basic sales and negotiation advice but not much that moves the needle in any situation.

I think that could be dangerous if people are not careful in their evaluation. 

My neighbor has listed his but also has had occupancy issues as an STR and said that most people looking for either rooms or cheap stays but I can't comment on that as I have no experience listing as an MTR.

My question is how do most people make the jump to the 2nd STR property if you're generating $25k per year on the high end? 

You can just have people rebook if they want.We bought our lake house for use to use on occasion as well.

Most people know this. 

Luckily for OP, I can't imagine too many people wanting to add 2 ADU's. 

There are 2 types of people who dog on Detroit.. 1.

But, people will always be able to see the prior listing history under the Price History section of the listing.