This is particularly for someone looking to grow a real estate business not just general posts. 

So I basically don't know how to swing a hammer, and I don't think I really have much talent (or natural interest) in learning construction? I plan on hiring a general contractor ( like many do) and then hiring my pro...

Mind providing more clarity on the asset you are purchasing and the overall business plan with making it perform? 

Rates: 9% to 13% (Most Deals are 11-12%)Terms: up to 36 Months (Most Deals are 6-12 months)Fees: 2-4 points(%) of loan amount paid at closing (Most Deals are 3 points(%))Minimum Loan Amount: $50,000 (For loans less than $250,000 $2,500 minimum fee)Max Loan: 65%-70% of After Repair Value(ARV)100% Rehab Financing Available (Require 20% of purchase price down payment or cross-collateral)Closing Timeframe: 48 Hours - 3 Weeks (Most Deals are 2 Weeks)NO PRIMARY RESIDENCES, NON-OWNER OCCUPIED ONLY, BUSINESS AND COMMERCIAL USE ONLY.

Quote from @Gian Pazzia: For properties that small, you should budget $450 per property and use cost segregation software like the one below from a trusted brand that has been in business almost 25 years.

Quote from @Gian Pazzia: For properties that small, you should budget $450 per property and use cost segregation software like the one below from a trusted brand that has been in business almost 25 years.

The costs for the LLC business will be paid with the primary business card.  

I have been looking at factors that affect where I would like to live (weather, politics, taxes, night life, etc.) but I am guessing that these don't necessarily indicate a good financial investment.

But since you switched to using it as an STR, make sure you've got all your dates and numbers lined up to take full advantage of this.Remember, every situation is unique, so it's a great idea to chat with a tax professional or financial advisor. 

I think HH provides these new home buyers the opportunity to purchase a home with some financial flexibility being able to rent out portions for extra income.