I am currently trying to break my analysis paralysis. 

RESOLVE this issue NOW and make a clean break. 

In your experience, do you find that it's possible to cashflow or at least break even with these properties and today's prices/rates?

We like the short-term rental idea because we could stay at the property ourselves when we want - summer break, spring/winter breaks, etc.Our budget will be right around $1M or less ideally, and we would like a short distance to the ocean.How likely is it that we could find a property as described above and have it cover or come close to covering the mortgage? 

As the investor gains experience, they are not only able to more successfully foresee the “bumps” along the way, able to handle recessions, temporary negative cash flow, unforeseen capital expenditures without panicking, but will also recognize the opportunities necessary to turn a loss into a break even.

Id be happy to break-even with the rental income if I get all of my invested capital back.

I personally don't see prices changing much until something seriously breaks.

It’s wise to start with breaking even and ensure you're comfortable with the costs involved.Happy to connect if you'd like to discuss more!

There is an offer to buy but if I include everything I've spent over the years, mortgage P&I, taxes, insurance, HOA, and recent repairs, I will just break even.

This news sent the deal’s value into a tailspin.At this point, I was looking at barely breaking even.