This is my slow part of the year, and I do all the things to move the algorithm…fiddle with order of photos, change seasonality in my photos, tick as many boxes as I can, fiddle with pricing.  

@Windu C. this is an easy ask. 

I’ve enjoyed hosting short-term rentals in the past and would love to share this home with others, as I’ve put a lot of effort into preserving it.

Electric, gas - Where I am at you can link multiple properties to one account this helps if you aren't doing that.

I see this come up on the forums from time to time and as a mortgage broker myself here are the strategies I implement to work with great lenders1.

Has anyone had experience with this issue and know a way to get a good insurance policy that doesn't cost an arm and a leg? 

The two units are currently accessible to each other by doors.

What made you interested in investing in this type of deal?

Is this what I should expect as newbie?

I would also talk to leasing brokers for this type of property to understand if there is real appetite from tenants for this type of building, as even if it doesn't directly impact your approach, it will give you some insights into how a potential buyer may be looking at it.