First, see if you can negotiate replacing the sale contingency with a longer escrow or loan period.

But in the meantime you could move into your new primary residence converting it from your 1031 replacement from the sale of your current investment.

It sounds like your current "strategy" is to react when bad things happen. 

This is the breakdown:2 tenants on month to month leases ~$250-$350 less than market1 long term tenant (15yrs) is now on month to month lease and is paying $1500 less than marketAfter consulting with a couple of people and doing some research, it sounds like anything over a I should apply banking rent raise and submit a 60 day notice (all of these units fall into that category).

Hey @Aubrey Adams - not to sound blunt, but there is no good time to buy.

It doesn't sound like you actually have an illegal unit here.... you have a two unit with a garden.

But you sound stressed (you should be) and without a way out.

And the rules surrounding replacement are much more relaxed.  

Some carriers offer loss assessment insurance, which can come into play when the HOA experiences a large covered insurance loss, such as a hail storm requiring roof replacement or a fire requiring building replacement.  

Water heater 12 years to replacement (may need some service before replacement).Recognize many cap ex items are years away.