My property manager then sent another technician who said the gutters need to be cleaned and recommended installing leaf guards around the entire duplex, along with larger downspouts and overflow guards, for a total of $3,013.

I had bids come in to clean the building out and they were 50k plus.

There is a product you can use on flooring that works well (rejuvenate)-try that first.For most things it is the actual cost (eg cleaning) or depreciated value (eg flooring replacement). 

Are BOTH the condenser and evaporator being cleaned often enough based on local environment?

Like Michael said, I would use a cleaner once a month to clean or biweekly, restock the common area items (like TP, dish soap, etc), and sign up for routine lawn and snow services.

We always start clean at the beginning of the month unless there is a real need to start mid-month.You will have to use the leases that are in place and can transition the tenants to your leases as each lease expires.

Then there's other factors to success especially in a heavy lift like this, some of the most important in my opinion are Being on site regularly to manage the contracting processHaving a lot of cash reserves - 'a lot' imo would depend on how thorough your current bids are and how old the property isYou mentioned it's bleeding cash now, whatever your timeline is for the property bleeding I'd double it and see if it still makes sense. 

It seems like it's something people do on the regular, and the lender doesn't usually trigger the due on sale clause. 

@Laura Ozols @David Tran @Mario FurmanczykHey All- I work for a company that provides PACE (property assessed clean energy ) loans similar to HERO. 

Operating Expenses:Consider all the costs of running a B&B and event venue—staffing, cleaning, maintenance, utilities, insurance, marketing, and supplies.