Use AirDNA to help determine a solid geographical area to maximize ROI & vacation desirability.

Most of them are estimating a construction time of 12-18 months.I have a few homes that are on large lots that should probably be further developed to maximize return.

Depreciation - You may be limited on how much you can take so keep that in mind and maximize cash flow to access as much depreciation as possible. 

Would it make sense for you to live somewhere else and rent all 3 units to maximize the income on the property to eliminate your debt?

They can advise you on the specific rules and regulations that apply to your situation and help you maximize your deductions while staying compliant with tax laws.

Additionally, it can help maximize renovations and improvements.A Cost Segregation study is an IRS approved federal income tax tool that increases near term cash flow by utilizing shorter recovery periods for depreciation to accelerate return on investment.

Also, from a marketing and revenue management position, hotels are better than many STR hosts at maximizing top line gross revenue with events and other specialized clientele. 

The goal of flipping a house is to maximize profit while minimizing the time and effort spent on the property.

My biggest concern is how to structure it to maximize positive benefits and good will without sacrificing too much "control".

You won’t be living here forever, so ideally having an exit strategy is key to figure out how to maximize your money when time to sell