And I keep my properties in good shape (and get them into good shape when I buy them) to ideally prevent issues before they happen. 

Then get your own place and rent out that unit.You can be local to the units you are taking on and prevent a lot of problems that happen with OOS.I agree that $15k is too low for you.

For instance, you could agree to cancel some of their outstanding debts, and/or you could make it clear that their security deposit will be withheld if they don't leave under your terms, and/or make it clear you will file a lawsuit to recover the money they owe you if they don't meet your conditions, and/or get a collection agency involved, and/or you can make it clear there will be an eviction for non-compliance with the contract (among many other methods)...I would also suggest reading up on cash for keys, and seeing whether that strategy could work...talk to the tenant to get an understanding of why they are staying, what things would prevent them from leaving, what things would incentivize them to leave, etc.  ...ultimately, you need to create a new agreement (in a new contract), where the option of leaving and abiding by the terms of your new contract is MUCH more appealing to the tenant than the option of staying and/or violating the terms of your new contract.  

I don't know exactly how that works and if that can really prevent her from selling her house so I didn't know what to say to her other than I was going to find out if I could help her in any way. 

Hoping someone can help me give advice to my friend.She is looking to buy her first house in Wisconsin. It is an old farmhouse in central Wisconsin, currently occupied. As it is in a rural area, it has a septic fiel...

This prevents the buyer from seeing the assignment fee. 

Not having all this discussed and agreed upon up front is how many partnerships end up in disaster --- although, having it does not prevent it... 

Utilizing experts’ knowledge can prevent you from buying the wrong investment property, one with maintenance, location and even legal issues.Read this article for detailed information https://www.forbes.com/sites/f...All the best!

They would charge less than $400 a month, have a solid lease, know the law, know the market, can deal with difficult situations quickly to prevent them from growing, etc.

Mail the air filters to the Tenants and make them change them.Your current method is OK for a few rentals, but it's not going to scale and I have to question the cost:benefit of it all.A traditional property management company doesn't have an incentive to perform preventative maintenance or to keep tenants happy, while the self-managed property owner has both.