Because, even though it's free to clean, people don't bother when they know they aren't getting their security deposit back. 

Property doesn't need a stitch of work and is super clean but for whatever reason they are selling below and off-market. 

I cant count how many times ive had to clean it up or replace materials. 

He has already had to void the lease renewal for one tenant/friend who could not maintain clean standards and has just renegotiated a significant price increase for the second tenant/friend who is falling into the same issue - can't clean up after his dog, clean his bathroom, etc.The point is, without a lease to use as leverage, my buddy would be SOL and left to his own devices to negotiate with the neanderthals he got into bed with. 

Generally if you average 7 or fewer nights or 8-30 nights and provide "substantial" services such as tours, house cleaning during a stay, meals, etc you DO have to pay self employment tax.Kudos to this CPA site (tarlow. com/2018/01/02/tax-ramifications-short-term-rental/):"When property is rented for short periods, special (and sometimes complex) taxation rules come into play, which can make the rents excludable from taxation; other situations may force the rental income and expenses to be reported on Schedule C (as opposed to Schedule E).If you have been renting your home or second home for short periods of time, here is a synopsis of the rules governing short-term rentals so you can prepare yourself for the upcoming tax season.Rented for Fewer Than 15 Days During the Year: If you rent your property for fewer than 15 days during the tax year, the rental income is not reportable, and the expenses associated with that rental are not deductible.

Does anyone have a cleaner they recommend for doing cleaning/turnover?

For two reasons:1) because of the synergies: you already have a cleaning crew, handyman, you know how to furnish these units, you know how much to charge, you know how to market them, etc.

My wife was there cleaning all day so I could show it to a bunch of potential tenants tonight after I got off of work from my job (active duty Army).

From what I'm putting together, once the banks acquires the property they take 6-7 months to clean it out and put it up for sale at market value regardless of property condition.

I helped him clean the place up last night and have plans to meet him and the potential buyer at the property tonight.