If it turns out you are grandfathered in, and the grandfathering occurs at the deed level and not the owner level, your house might be worth more than it is worth right now since you own a home that can be used as an STR without the regulations.Mike

Plenty of agents do that are high level networkers.

Not sure what metrics you have used in penciling down this market but make sure you look at population growth trends, income levels, poverty levels, Job diversity, schools etc.

My advice would be to level set your expectations of a property first and what your highest priority is and then work towards finding a property that meets those expectations and gets as close to the 1% rule as possible.  

Lot #1 is a .75 acre lake front lot with a 4 bed 2 bath split level built in 1974 with an attached garage and 100ft of sandy shoreline.Lot #2 is a . 75 acre lake front lot with a 2 bed 1 bath house built in the 70s, a 30x30 detached heated garage all on 80ft of shoreline.

I pick my own hours, pay is 1099, and each game is between $40 to $140 depending on the age level.

They were built in 2010 - 2012 and are stacked on three levels.

However, at this stage, I just want a high-level check on whether I might be in the ballpark. 

Since the the LLC is owned only by my wife and I and the previous property was only owned by my wife and I, at a federal tax level, there is no difference in how it would be reported on our taxes since we file jointly. 

Customer dissatisfaction leads to less than 5 star reviews, too many less than 5 star reviews means you won't rent very well - so if it gets to that level - whats the point.