Shoots I have similar questions... we have a lot of folks with vacation rentals, but most of our business entities have acquired land over the last few years and are holding it for development... but it's very hard to get that ball rolling out there!

If so, refinance and roll. 

You rolled the dice and lost.

Looks like you are from Dot, so even though a lot of the 3 fams you may be looking at are pricier (aka 800/900), the rent rolls on can hit 8-10%+ CoC returns because the rents are so strong.

I checked online and they had terrible reviews but after reading them, I found out it was people who were pissed off they don't sell/promote California rolls or Spyder/Rainbow/Whatever rolls there.

My understanding of a 1031 is that you have to own a property a year and a day in order to roll the equity into something else. 

Would it be better to list the unit for longer term rent, or roll the dice with the Airbnb route?

The $500K exemption might not be enough for a lot of people...this is why this is all so regional  many parts of the rust belt the values peaked 20 to 30 years ago and have been eroding ever since.. so get that they don't have the same upside all the west coast folks have .. nicely bought west coast properties especially if you built them yourselves will be plenty of money you don't need rentals.. you get tax free money when you sell then keep rolling it.. that's what many builders do .. and I know I have done it 6 times since I bought my first home in Silicon valley in the late 70s.. and I am just one of millions of other west coast owners who have done the same.. and of course those that bought rentals on the west coast plus their homes have serious equity.. those in the mid west or rust belt the only value proposition basically is cash flow and number of doors since they really don't get or have gotten meaningful appreciation..  

We have lived rent free that whole time, currently equivalent to about $40k/yr in rent, and now have around $100k cashflow before non-routine maintenance and repairs on a rent roll of over $200k, with a net worth of around $4m.Number of doors is not everything.

My boss is a GC and he rolls his fees into the rehab project as part of the partnership profit in the deal.