At a very high level, if you find a seller that needs to move quickly and is willing to sell at a deep discount to get what they want, then that's step 1. 

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.

I'm not your lawyer, so you know, I don't give legal advice, and things I say you should consider stupid internet rumors.The way that statue reads to me is... you can really do whatever you want with it, but if the tenant files a demand for it and you can't product it in the needed time, you'll end up owing them triple the deposit as a penalty, so you should probably make deep considerations on the risk profile, as if you can't produce it quickly, it gets even more expensive, very fast.

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).