It’s listed for sale on all the home sites(Trulia, har, Zillow etc) If anyone has time to go take a look at it and based off what you see in the pictures and give me thoughts and what they think something like that could be built for.

I assume you could take a similar approach with Redfin, Realtor etc etc.There are STR sites like Rabbu that present deals regularly but not sure if these are sold furnished. 

I find the rental application tailoring or modifying to be a lil cumbersome on the site even worse on the app.

I am both an investor and realtor so ideally, your best bet is to find someone like me in the Cleveland market.

Advertise the property on Craigslist or other sites if you must. 

In my experience, your best bet are local, community banks.

DSCR mixed use would probably be your best bet and give you the best pricing! 

Starting smaller is fine, but the unit has to be spa like or you will likely fall victim to pricing wars or get lost in the booking sites algorithms. 

Long term play, this is likely your best bet.

Sure it can be a write off, but my question is if it is the highest and best use of your time (or the given employees time) to be running a skid steer - transporting it, storage, maintenance, cleaning, etc, and if it still makes sense if you need to hire someone to run it for you and take care of the other things.Add up all those recurring costs - maintaining the machine, maintaining the trailer, having a large enough truck to tow it, insurance and registration for all of the above, your time or your employees time related to all of the above...even at $14k a year it might be attractive enough to keep paying that and having them drop it off at the job site for you.A brand new machine could easily cost you over 6 figures - that's 7 years of rentals at $14k/year before including all the holding costs.