One of the biggest complaints with DSTs is the high cost/fees associated with them.

No matter how you decide your other questions please make sure you have an Exit Strategy in the partnership agreement you end up with.

We have had only one in 15 years over the entire portfolio (granted we rent higher end, so less drama to begin with) but if our team can't fix an issue I usually meet with the tenant to find a solution. 

One thing I'd keep in mind with mid-term rentals is I expect the mid-term rental market to get highly saturated at some point just like the STR market has.

I think it’s worth it for just a week or two after the current MTR booking ends.

Luckily, real estate is highly forgiving.

Or would it be jumping into the deep end prematurely?

Especially if you have a short high season which is also the time that you want to be there.

I wish I had all my mint data for some end of the year tax reporting, and am not scrambling to find something new.

It ends up being around 1,200$ a year just for accounting only with QBO and thats way too much and it isnt really geared towards rentals.