@Patrick Mortenson just because county has assessed an increase in your property doesn't mean your value is there.

It seems to me that you would rather a secure financial position than to leverage your assets to make to increase your cashflow.

Adding an extra room would increase the value of the property and can be rented for an additional $500 more.

I also increased my monthly expenses by 30% (vacancy 5% of rent, maintenance/cap ex 14% of rent). 

Was able to increase rent.

If you are flexible enough to allow a little more time you will reduce the chance of damage to walls and woodwork (happens when people try to move things too quickly) and increase the chance of the place being left at least empty and broom clean.I would trust but verify. 

Just do the normal annual rent increase and he should be more than happy as a "good tenant".M2M is best option for a landlords and has no disadvantage to a good tenant.

The crime rates in some areas are still high but as  job outlooks increase and diversify I believe within the next few years we'll see quite a change and upward tic in profitability.

Increased rents but $250 in one unit and will increase the other when I move into my next deal.

Then I look at the level of increase in taxes and pensions.