If one is a duplex and the other a single family home...I'd bet the single family home is the better one to sell. 

What are you offering in exchange for the capital?

I sold one of mine last year to a gentleman from out of state who needed to do a 10:31 exchange, and he ended up just moving his son into the place I would recommend advertising on local and even out of state Facebook groups.

If Newburgh sees valuation like Beacon did there still could be opportunity, however like I mentioned the people betting on this already did it years ago. 

The 1031 exchange seems daunting but it is not.

Using strategies like a 1031 exchange allows you to sell and reinvest in another property while deferring taxes, so I often factor this into decisions.For me, it's a combination of interest rates, appreciation, and potential cash flow.

Furnace was 30 years old and there were cracks in the heat exchanger.

But, I would not bet on a boom in rents or prices until 2026 at least. 

Are you paying more in origination costs in exchange for not having a prepayment penalty?

Most people will tell you that your second choice can't be done, but the IRS has issued two (2) Private Letter Rulings on point where they did allow the taxpayer to build on property they already owned through a 1031 Exchange.