She said she couldn't stay in the house for that long for reasons that the house has children and it was not clean (she kinda hinted it during our conversation).

Longstanding local businesses, clean and attractive landscape, military etc.  

Originally posted by @Kay Kay Singh:@Maverik Eaton get out of your comfort zone and pull the trigger because nothing grows in the comfort zone.  ...and if you don't plant the right seeds, or don't clean out the garden, anything (weeds) will grow...and out of control.Stay in your comfort zone...just grow it larger.

I plan on keeping it forever as a rental so I didn't care.I can clean up the title later if I choose to.

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?