@Joshua Strickland, @David Bergmann, @Sofia Sharkey:Do you guys have a software recommendation to manage cleaners?

It will be much simpler, cleaner, and less risky, to just buy the house from the heirs and then do your rehab. 

Be sure you and the cleaners have the proper insurance and bonds in place against theft and claims of theft. 

I would be inclined to order a deck cleaner/wash, a deck paint of your color preference, and general paint/staining supplies (brushes, rollers) from a nearby Home Depot/Lowe's, pay for them, and have them available for pick-up by the tenant at the contractor's desk. 

These are cabins in the woods, so we have issues like power outages, neighbor's construction noises, internet outages (a big deal when people are planning to "work from home" at the cabin), guest thought they reserved two nights when it was only one, cleaner forgets to show up... all sorts of things that add up.It seems like the littlest issue gets compounded into much larger issues that cost us lots of money.

Don't be a hack and try to take him to the cleaners. 

Find great cleaners and pay them well.

You said you have good people to clean and communicate so I was curious if you have your cleaner do that part.

@Tina Rubin as an occasional lender myself, I think the second option (new deal/property) sounds a little cleaner and more of the traditional lending scenario - if I’m understanding you correctly.Just make sure you have a good understanding of the higher rate you’ll be paying to the HML and make sure you can still make your numbers work with that higher payment amount.A hard money lender’s main concerns will be the value of the collateral relative to the loan amount (LTV), and whether your estimate of the project cost is accurate.The HML will definitely want you to bring a substantial amount to the table as a down payment to keep their LTV low (65-70% is common), so if you need to refi your current property to get those funds then that might be something you’ll need to look into.If it was me I’d probably stick with a traditional fixed loan on the first property and start out with a private/hard money loan on the second, until it’s rehabbed and stabilized, and then refi out with another bank loan.

Is anyone here familiar with a good STR cleaner in the Daytona Beach area?