What type of premium do you place on a furnished and turnkey str?

Marinate on that.You put up a temporary wall.....get a renter in either side of it....a;; it takes is one disgruntled tenant to do a public records search....see that you have an unpermitted bedroom there and you are on the next episode of "Landlords dealing with nightmare tenants.".Either leave things the way they are and charge a premium for an extra large room.....or get the "extra bedroom" permitted and then keep it moving. 

Hello,For the past couple of years, I’ve just been filing my taxes using TurboTax premium.

Another good point to look at is are there any repairs or improvements that can be done to charge more of a premium for the rents?

Of course if you know what your new property taxes will be, or insurance premium increase, then factor those in as well.  2.

They had looked for a home in our neighborhood that met our specs last year but shut down their search due to crazy market conditions and are now trying to find off-market properties - even if it means paying a premium.

Cash out, multifamily and non-owner-occupied loans all carry higher risk of default, so you'll need to have a strong profile (credit, income, some reserves) and otherwise and pay a premium in rate. 

On the other had, it the guy whose property is doing $50K decided to sell how, he/she would build in "price premium" for the fact their property is doing so much rent, which would actually diminish the cash flow potential for the next buyer.

If you are the only owner in the LLC you can also do the umbrella under your personal name and adding LLC as additional insure which is also typically lower in premium. 

By limiting the # of carriers, you premium will most likely be higher with whomever you move to.I suggest either removing all of the grills now or try and change insurance carriers before your renewal.