I am wondering how much expected weather of an area impacts your decision to invest in a specific area.Recently looked at Census data which shows that people are predominantly moving to Florida and Texas.

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

Always be cautious of what you charge on things like paint, flooring etc.. most judges will use life expectancy and divide out a pro rated amount you could charge the tenant for excessive damage and not normal wear and tear 

I expect my cash on cash return to be over 90%.

While I could have gone lower I am lowering my risk tolerance because I expect a recession in late 2019 to 2020.

Also know that building a home seldom goes as expected - I have relatives that just built a nicer house… they thought it would take 9 months… it literally took 18-24 months between delays in permitting and the builder just not being able to get it done in a timely manner - often due to sub-contractor issues.  

W2 and 1099 income, 2 kids, renting, and 1 rental.At what point does it make sense to hire tax help and how much should that expect to pay?

Not the cash flow play a lot of people expect. 

Properties here often fall well below $150k, and the market is expected to see home prices rise by 10.5% in 2025.

Quote from @Andrew Steffens: I think going into an STR purchase with reasonable expectations of cashflow in this current market and rate environment is admirable.