They are a young engaged couple, and we actually have a few acquaintances in common (a connection we discovered when they were moving in). 

All of my properties (8) are between 50-100 years old and I’m confident are worth much more than a new structure in a cheaply built community.

This is appealing for short-to-medium term gains, especially if you’re confident in your ability to refinance or sell in 15 years.

If there is an area where you are not as confident like plumbing, electrical work, etc... then you can always find a subcontractor for that. 

I have done my research and feel confident the properties will still cash flow with Long Term Rental rates in the area, but will cash flow a much higher rate if the STR rates on the estimators are accurate.  

For his second approach I can confidently tell you it will cost you much more money, and cause several delays.

We know how tricky it can be to find legitimate sponsors and solid deals, so we built PassivePockets to give you the tools, resources, and community support to help you invest with more confidence.

They are an engaged couple, the guy’s mother, and the woman’s brother.

I'd probably get multiple feasibility studies before engaging a bank and/or spending any money on the actual project.

With over 20 years of being in the trades, I am very confident in my abilities within the industry.