If it's vacant and really needs cleaning/repairs, then I'll wait until it's more presentable.2.

Commit to spending less, paying off high interest credit cards, maintaining positive cash flow in your personal finances, and cleaning up your personal balance sheet.  

Hey @Devin Bost, I would highly recommend a few things to help with this. 1) Have systems and processes lined out for any emergency you can think of.2) A spreadsheet of subcontractors/ vendors that could handle the situation that arises (plumbing leak, electric out somewhere, etc.)3) Your cleaning team and handy person should be utilized for some things.4) Something like Breezeway can give you 24/7 support around your property with a dedicated phone number line.

But in a rooming house, they pay a much lower rent cost, and get the benefit of a professional cleaning crew doing common areas, kitchens and bathrooms, free high-speed Wi-Fi for their streaming devices, etc.

Both are on autopay, have insurance, keep their places clean, and are civil to each other.The upstairs tenant is a school teacher in her late 40's. 

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. 

To date, we've cleaned up the title issues, maintained the land/property, and worked with the City of Kansas City to determine a new highest and best use based on the revised Midtown Plaza Area Plan.

They should have just cleaned it up and listed it for 70k.

I also have a close relationship with the cleaning company, so that part is covered. 

I think you're gonna see a lot of deals underwater trading before year end, with banks trying to clean up their balance sheets.5.5% with 25% down is a very competitive rate.