You could spend a fortune retrofitting your house depending on what needs to be done, and I would bet that if you had 10 different engineers look at it, you'd get 10 different opinions.

I was doing some reading and learning and have come to a conclusion that maybe my best bet would be to sell on a Land Contract gather what I can from those down payments and possibly create just a little bit more cashflow and use it to put down on an actual cashflowing property.

If that is the case, why don't insurers take them into account when calculating premiums.

With renters; you bet.

You can bet he'll be even less responsive after you've agreed to do business with him.

Your best bet is a small local bank.

If you bring a polite attitude and a spirit of refusing to accept no, I'd bet you'll have some success.

The right choice is perhaps dictated by whether you want the benefits of current return or want to bet on future value.

Is there any leeway in terms of having the home on the market (and not used as either a rental or primary residence) when calculating the 2-of-5 years for the capital gains exemption?

You don't need a calculator or even a pencil to figure out that the best move here is to just not pay the taxes on this parcel and let it go.