For the cold weather folk that are do it yourself types.

Then you pay for clean up, repairs to get ready to find another tenant.When everything is done, repeat all over.Ps - roof life 10-25 years depends on the weather, woods around and materials- furnace 25-30 years- HWT 10 yearsEtcNow factor these money into the price of the house and get it inspected how old is the major parts.

Or just holding on for dear life and weathering the storm?

If you're able to weather the stupid stuff that happens, you'll make it.

My rentals are inland in Columbia, SC, area, but anytime there is a major weather event I send reminder emails to my tenants.   

I even looked Upstate, but decided didn't want to deal with winter weather and Property taxes in general in NY state are high..

So, given that there was a crash 10 years ago (and some people forecast another big one soon) and there are plenty of investors that do ultimately fail in healthy economic times, what does that look like, and how do you recover?

I used to dive into conversations like this, but I gave up “forecasting” years ago after my crystal ball had failed me so many times.

Although you could refinance after a little more than a year (assuming property values stay the same) into an 80% ltv loan, a lot can happen in a year (tenant moves out, roof needs to be replaced, economic downturn, etc) that you need to weather.

Though I can understand why you want to do the work before the weather and holiday season sets in, those types of deals are fraught with problems.