The stairs are about 16' from the fireplace and the heat is disconnected. It would take a lot of space heaters to be able to detect any movement.
You would see it as an onetime experiment. Run them for an hour or so and see at the top of the stairwell if you can feel warm air coming up. Depends if your circuit can handle it. May cost a few $ in electricity but buying a wrong-sized stove will be much more expensive.
I'm just hoping to supplement my oil/cast iron baseboard heat in the living room, dining room and kitchen as well as the basement. The bedrooms are on the other side of the house and I'm not expecting to do much for them. Although, I have toyed with the idea of putting small vents and returns up through the floors of the bedrooms with small muffin fans helping airflow. I don't like the idea of cutting holes in my oak floors though.
If you spend most of your time upstairs, putting an insert/stove there may be the better option. With some well-placed fans you may be able to distribute the heat across the whole upper floor. If you like you can post a floorplan for some tips regarding heat distribution.
If you put vents in the floor make sure they are compliant with your local fire code.
Here's a question... if I buy a larger insert with the hopes of heating the upstairs and then find out that it's not working, will I be able to just use less wood and close the air vent down so I don't cook us out of the basement? Or are there limits as to how low you can go?
You don't want to close the air control so much that the fire starts smoldering. What you would do is to put less wood in to make a small, hot fire and probably not run the stove all the time. Not the most efficient way of running a large insert, though, as you will spend more time with small startup fires to heat up the stove and flue again. Potentially also higher risk of creosote. Dry wood will be key as usual! Do you already have several cords of wood split and stacked in your yard for next winter?
Another option to think about: Get a medium-sized insert with a firebox of 2+ cu ft for a consistent overnight burn (meaning you will still have enough coals in the morning for an easy relight). The Osburn 1600 is a tad small in that regard. If during the first winter you feel the heat is going upstairs and you would benefit from a larger insert, sell it and get a larger one. You still can use the liner then and probably do the install yourself with some friends. How large is actually your fireplace?
Regarding both options you may potentially spend more money than you need to. Buying a larger insert and then only running it with small loads would be a waste. Buying a medium insert to swap it out for a larger one soon thereafter would also cost you more. It comes down to what has a better chance of working right away in your opinion.
Some tips regardless of insert size:
If it is an exterior chimney definitively use an insulated liner. Draft will be better and less risk of creosote. For an interior chimney it is still highly recommended.
Have a sweep clean the flue and take a look at its current condition.
Put a block-off pate in to keep the heat in the room:
https://www.hearth.com/talk/wiki/make-a-damper-sealing-block-off-plate/
If the fireplace is at an exterior wall think about putting Roxul behind the insert:
https://www.hearth.com/talk/threads/finally-got-around-to-insulating-my-fireplace.75755/
Keep reading and posting around here for more advice and help.