I will likely have to sell the property since the rent can't support an extra $291/month in taxes. 

My brother is lucky because thats not the case but I  would hate for him to be considered a charity case just because he's trying to earn a living.

I wouldn't put forth the extra effort because an increase of $50 on a $2095 rent wouldn't be a hardship whereas a $500 increase on a $2095 rent might be.At the end of the day, I really do think its market dependent. 

This way they don't have to move and you start earning money next month.

In which case, your extra money might be better deployed into getting more deals.Actually, that would be my suggestion - pay the highest interest rate (for the ones above 5%) till you bring it to the point the principal/interest ratio is substantial (like 80%/20%) and then stop - the note itself will act as asset protection.

Would you also advocate the tenant pay for repairs or paying extra rent ?

The lawyers that we've gone to are telling us that we are required to pay for them to open an LLC and put the home in it (lawyers are saying the paperwork for an LLC is $1k) and we are trying to stay simplified and not pay the extra amount for the LLC so we can take action on the real estate deal. 

I am not afraid of virgin territory and thankfully I don't depend on earned income for a living. 

You will be seen as more respectable & will also have more ways to earn money.

I'm in Central Oregon which is one of the hottest and fastest growing markets in the country and that has a lot of people feeling optimistic, but I like what you said about those extra expenses and how quickly they can add up.