I live in CT and wanted to make sure this would be enough to at least pause it considering he didn't send it to my home address.

There are many people that make money in real estate in CA.  

Any insight on whether the ROI would be worth it or other considerations I am missing would be much appreciated.I have a similar looking 3rd floor space that I just finished making into an office/bonus room.

I know that I am not the first one to make a post like this so I understand how bringing value to the table can differentiate me from someone else in a similar situation.

Nothing is less seasonal than Orlando/Kissimmee, but it's heavily saturated with STRs here and difficult to make any real money these days.

Don I have spoke at many of these events.. the one here in Oregon though I personally dont care for much.. they tend to bring in old retread type guys that are pitching systems that worked 25 years ago.. and I pretty much believe they are taking kick backs for the sales those guys are making..

I’m a buy and hold as well but if it doesn’t make dollars…I also factor if the neighborhood is growing, is anything bringing appreciation.  

There has been some hesitation for me to sell due to the fact the rental market here is averaging $2,500 in rent for my area and property, I make great money now and have funds to cover vacancy and repairs on the home, but I would like to be able to afford a nice rental for my fiance and I to live in while we save for our primary residence.Shoild I sell and take my profits (60-70k net) and throw into an investment closer to where I will be living or should I rent, cash flow and build equity in the property. 

Does anyone have an idea of the who I could hire to make drawings to submit for a permit?

Make a good connection at your home improvement store/outlet whatever it may be.