So the increase in revenue probably ends up being 5-6%.Maybe I am over estimating the cost though.

Purchase price: $80,000 Cash invested: $25,000 I helped my father-in law convert his LTR to a STR recently (he's owned it for forever, but we wanted to see if we could increase the revenue by switching strategies and updating it).

I need to create some kind of significant revenue stream to ensure my wife, kids, and grandchildren are taken care of when I’m gone.

The last part is the biggest challenge.

The deal will be my biggest deal yet and is in fact a large deal.

What are the biggest challenges you’ve faced with either strategy?

It is the biggest cost/challenge for making rentals work in my opinion.  

Learning about dynamic pricing is a great next step to boost your revenue by adjusting rates based on demand and seasonality.

The biggest hurdle, is validating that you will not live in it.

The revenue difference between like-kind homes that have the design and those that don't is stark.Like others said, counter with a flat fee.