My Father has been renting us a house in OBX every summer since I was a kid and were both pretty affluent now and I'm floating the idea of us going in together on an Oceanfront somewhere in OBX that we can use a few weeks a year and have it pay for itself via rentals the rest of the year. 

You can turn always turn the home into a rental but at origination, your intent must be to live there within 60 days.A twist a lender can answer: The service member will be living there in 6 months but the spouse and kids can go early.

Supplementing her SS with rental cash flow income may be enough for her to go enjoy life to the fullest AND leave the legacy for her kids and grandkids after she’s gone (that’s also very important to her). any thoughts, experiences and nuggets of wisdom are welcomed!

You should just get started; don't get into analysis paralysis trying to find the perfect strategy.The only downside here is that you will be doing a lot of moving, so make sure the family is on board, or else after the second move, you may be spending all your profits on a marriage counselor... just kidding.

You could spend weeks trying to get a complete application from the three college kids, only to see them back out and rent something else.My policy is to accept applications and process them only when they are complete.

Are you kidding me, your entire investment is based on using the property for short-term rental - any complaints by neighbors and you have to cease.

Lol I was kidding, Bryan is a friend

Easier to rent:  Two bedrooms attracts fewer occupants (not tenants) vs a 3 bedroom where often that extra bedroom is housing an adult kid, dead beat family or friend.  

The martial arts helps kids in so many other respects than just the self-defense application so it's not all bad.With the arts you have to train for a very long time to take complex movements and make them part of your natural reaction process.

Someone took the little basket that holds soap and shampoo and the sign on the back of the toilet and placed them waaay in the back of the bathroom cabinet.Someone removed the tiny little LED lights I have on this 8 foot tall fake ficus in the kids bunk room and put in on the deck.