@David Desousa,I'm going to disagree with the idea of leveraging into a more expensive "better" property mentioned above.

Either of them make the rules and they've found that the lower loan amounts either cater to a borrower that is distressed and can't buy a more expensive property (they're riskier) or the amount of time it takes to originate/close/service isn't profitable. 

You can't just change the terms of her lease unless she agrees as well.I'd say to her, "apparently you aren't happy here, so if you would like to find a more suitable place, I'll let you break your lease with no penalty".She's done a pretty good job of getting you trained and if you don't put a stop to it, it will only get worse.

Condos are a more viable strategy and there are some associations where the numbers work better on as rentals, but you might not find the "2%" rule even looking for that type of property. 

I can 100% tell you why I use property management companies-https://www.biggerpockets.com/blog/2013/06/29/prop...That's a more dramatic scenario, but a more basic reason is- I hate landlording.

You either need to vote to amend your covenants (not bylaws) to a more specific explanation of what is allowed OR your board can create a "policy" that further defines and explains generator use and when it is allowed and what happens to persons who violate the policy. 

@Thomas Meyer  I would like to do a more cost effective solution like that next time I have a vacancy, but these people were so determined I'm not sure if that would be adequate.

There's a direct relationship between your work and the additional payoff here, and some people are okay taking on a new job, while others prefer to spend their time in other ways.If you prefer a more passive investment/hands-off approach, then you can invest in notes, if you know and understand that space.

@Javier Gaillard,Metro Detroit may be a more steady market but Detroit better cash flow.

That being said, there were definitely times, both from a numbers standpoint, as well as an ethical one, that I advised clients to go with a more structured route.