Deep down, he worries he’s not successful, confident, or attractive enough to "deserve" a beautiful partner.

Not alot of confidence in any existing rentals as consistent indciators but I feel like so many homes are 1/2 rentals and don't tell the whole story.Anyone have any insight into the Cashiers/Highlands/Sapphire/Lake Toxaway markets to share? 

Self sufficiency rule makes 3-4 units almost impossible. 

Morning Nathan,Congrats on exploring a big jump-it takes courage to buck the news cycle and confidently reach for a bigger future!

For pros/cons of booking.com I would say the following...Pros:-if you use guesty you can sync your airbnb info into your booking.com listing info to ease the set up process-there are more options to check off in the amenities portion of the listing set up, so you can really display the uniqueness of your property-I would wager 90% of self-managing str hosts only list on up to VRBO/Airbnb, which means there are not nearly as many options for people to choose between, which means more exposure for your listing-rumor has it that booking.com just invested a large sum of money into building out their services to provide more vacation home listings rather than hotels.

In my case, I have residential rentals in one LLC, commercial properties in another, self storage in a third, and my real estate company operates in a fourth.

Than learn with that safety net until your ready to take things back over to self-manage again. 

I am passionate about Tiny Homes, I started just by helping more people with creative floorplans by self teaching myself CAD design so I could help more families.

So often rentals don't have taxable income; and once they do it's still not subject to the payroll taxes paid by W2 wages or on self employed income. 

We wanted to self manage.How did you find this deal and how did you negotiate it?