With social media, yelp and the power a consumer has, you can only screw so many people over before you go broke and lose your customers.

There are a select number of homes in the 2 million dollar range and up that do produce positive cash flow, but those are newer oceanfront  homes with tons of amenities and upgrades and the maintenance and upkeep is brutal to keep up with the demands of that higher end rental customer. 

We can assume its one time, but that's a dangerous assumption to make maybe he pays that to his brother-in-law every year instead of an XMAS gift.

I made some other assumptions, but I'm seeing mid single digit cash on cash return and not enough cash flow.

I want the name to be creative enough to grasp the interest of our future customers, it has to be memorable enough for them to consider is as their first choice when in need of a contracting service the my competitors provide as well.

"Assumed" in this case means I owned the property jointly with another party (i.e. former spouse) and went through the assumption process to remove her from the mortgage and deed (the paperwork is similar to a refi, with fewer closing costs...and a bit of a lengthier process).

However, I would encourage you to build a custom model to reinforce the basics of underwriting and forces your to understand the big picture + granular details behind the "Why". 

Or is there an online service that I can somewhat customize a lease that way?

List building can be as simple as driving around your target area for prospects, or, buying customized lists of prospects from sites like Listsource. 

So I am operating under the assumption that this is worst case scenario,  and statewide will be more moderate  (if moderate could be used as a term for rent control) - so if we have to have it,   I'd rather it be passed statewide.