I think demand will continue to grow as the area settles into its next life as more of a year round destination.  

At some point, the juice isn't worth the squeeze for us and we just want to enjoy life. 

We’ve worked together for about 2 years now, and he is focused on the operations side of the business.There are many solid sponsors and operators in this asset class, some newer than us, and some older – and quite a bit of new money coming into this space (part of this is where we are in the market cycle, and other asset classes being overpriced like apartment buildings).I’ve personally had several conversations with @Jefferson Lilly (and met him at a conference), and he knows the space well.

Building relationships with them early is key.For tenant communication and rent collection, tools like Buildium or Avail can make life easier.

When you move out you begin to experience POSITIVE CASH FLOW in which your tenants help you buy the property.....where eventually you own it out right, and now it becomes like a pension..........Predictable and Sustainable income for life.   

It frees you up to focus on living your life and acquiring more property.

I've been a real estate investor my entire life, doing my first deal as a senior in high school ($5,000 mobile home).

I'm not a huge fan of constant buying and selling - it's just too much damned work at this point in life - but for sure I would jettison anything that wasn't making an acceptable profit, and if you have any RE you should know this number. 

With current interest rates, and they are at least 1% higher with potentially additional points for non owner occupied property, it is hard to find properties that will allow for positive cash flow after paying the mortgage, if you are looking for money for the down payment from a private lender, those are normally at higher than market and I am not sure it would be possible to pay it off.... please remember you need to take into account that you may not have a tenant for a certain amount of time, a tenant may stop paying rent, or you will have a big ticket item to fix, so I would wait if I were you and save to have enough for the down payment and closing costs and perhaps some money set aside for repairs. you also want to make sure that you have your own emergency fund outside of the money needed for the investment property because life happens ....

Don't make your life more complicated than it has to be.