Marketing is a 3 legged stool of Market, Message, Medium.

She lives with us, and she really has little to do with the homes; I do all the day to day management and landlording.The two houses are rented, and generate a gross of $75k a year for the trust.In the medium term future, I'd like to purchase another rental SFH or small MFH and have it placed in the trust as well.  

A good pivot strategy for short term rentals is medium term/corporate/furnished rentals.

My understanding is that I must pay the TDT tax for any booking under 30 days but bookings over 30 days are considered long / medium term rental. 

Check out "piercing the corporate veil" and you will quickly see why the Umbrella policy is preferred for small to medium size landlords.

Small (residential) multi-families are reasonably easy to come by, medium (commercial) of 6-50 units are more difficult to find.

We are planning to acquire a medium-sized multifamily in the next year or so.  

Stick to medium sized communities with great demographics.

•I went to an absolutely awesome STR meetup last week hosted by Janine Whittaker and Jeremy Wirths and had a few conversations with folks and the idea of potentially doing a medium term rental in my current unit was introduced to me for the first time and is something that I have been thinking about since then.

I need an estimated 70-100,000 to facilitate this flip.I need to buy a plot in SD, move the home to the plot, do light-medium renovations to pretty it up, and then flip it.