We service everything ourselves (because we're cheap right now--please don't judge us too harshly).

Of course this would be harsh on the current owner, but this process is bad enough that it discourages participation which would result in lower prices (if there were not inside buyers).BTW drones are handy on virtually all properties. 

The larger unit will have higher maintenance/cap ex even with coastal environments being harsh on some items.I suspect your expense estimates are far too low especially if you kept the BP calculator default percentages.  

This is the harsh reality (at least for me) to get where you want to be.

NONE of these "ands" is a guarantee so it mathematically is incorrect to call it a numbers game.it is NOT a numbers game.The harsh reality of the matter is you need to think, and stop accepting opinions from others just because you want them to be true.

I generally advise against townhomes and condos as the HOAs can become harsh and limit your options.

Considering you have just bought this property and inherited the tenant, I would also consider finding some ways to be in good standing with them before proposing the rent increase, they might not take it so harshly.

It's a harsh reality. 

This is usually too harsh for a single incident, particularly with a new tenant.2.

Even if I raise it from $600 to just under $1200 in the span of a month the tenants have no where to go because I will still have the cheapest rent in a 5 mile radius.Though, I don't want to be too harsh as I have been in their shoes before, I will work with them on the rent raises.