@Jamie ParkerYou really need to do a more thorough job on the comps and see why did one sell for $150-$190, that’s a huge spread

We've bought off of signs on the side of the road listing a property for rent - we called the owner up and said, "We know you are looking to rent it, but would you consider selling it?"

As mentioned it will often be hard to sell one of the properties before the entire loan is paid off. 

right now I have a property that is in need of a lot of rehab. The roof is caving in and a lot more. I’m not seeing any comparables listed or sold in the area recently in this bad shape. the last lot I posted for sale...

HMLs are ideal for value-add strategies, where investors purchase, rehab, and then reappraise the property to pull out equity and reinvest, or to sell the property. 

I hold land personally with my wife that I am selling and at the same time I am purchasing my first str.

For a construction(or bridge) loan, most lenders would want 2-3 projects(buy, rehab, hold/sell, construction) experience usually in the last 3 years minimum.

Do we, for example, sell our current SFR and put all/most of the equity into a down payment on the duplex and have a lower monthly mortgage payment?

If they were to sell it on the market at a higher price and interest rate the numbers would not pencil out for me to rent it out. 

In many locations, including some of the other hot-housing market cities, appreciation has made homes unaffordable to those who don’t own a house they can sell for the funds needed to make a move.