Also contemplating whether to include a contingency in the offer on getting the city to approve the tree removal, though it would likely take a while to get the permit back.

I work in Middletown and the options I’m contemplating are below:1) House-hack a duplex using an FHA loan so I only have to put 3.5% down.

I truly resonate with this equation when contemplating my multifamily journey. 

so, i'm not sure what you were contemplating, but if you just go buy a solid, on-market deal that doesn't need a lot of work and put it under property management (as you should!)

After moving into our new home, we are now contemplating what do to with our first home.

., with municipalities in CA unable to prosecute car theft, robberies, assaults, rapes and even murders, I wouldn't hold out much hope with people hanging out.

Given the fact that so many people have jumped into the STR market, as if it were the next gold rush, even traditional vacation destinations must be contemplating regulations to protect at least some work force rental properties.

@Matt Ess, A very common strategy for investors wanting to defer large gains on their primary residences is to do exactly what you're contemplating - move out and convert it to an investment property for a year or two. 

I've never been shot, robbed or assaulted. 

So far we have been underwhelmed with the service and are contemplating taking our loss and handling it all ourselves.What is your advice on simply handling these things "in-house" or "manually" instead of subscribing to a software?