Tenants sometimes break up with a bf/gf and ask them to be reprogrammed with a new PIN.

Side tip, if you decide to close without using a agent (not usually a good idea in a new market) then you need to 100% get an inspection (using your own inspector, not the listing agents) and be there during the inspection, title insurance (as always), and have a pre-existing relationship with a property manager.

I'd work on getting them out and finding a new tenant. 

I am not new in RE (Own 2 (condo+townhome) +primary home) and all units are in San Diego and know want to buy something near beach and been in Imperial Beach lot of times love the place :)Any guidance how should i approach?

I am a new investor planning to owner occupy my first multi unit property.  

The tenant requested an extension to find a new place, so I granted a 15-day extension with a new end date of July 15th.

My tenant of 29 days is asking for a month to month lease so she can find a new place due to roaches.  

Although market fluctuations and regional differences can impact these trends, targeting the late fall and winter months usually provides a greater chance of purchasing a home at a lower cost.

We plan to sell this home and buy a new primary residence next year.

Need a new roof in a 3-5 years, you probably want to be pretty liquid (year long CD, Money Market, maybe very short term bond fund etc) for those funds.On a condo board 15 years ago, I  was once able to get us into some nice CD's a decade ago that laddered with the useful life of components.