Quote from @Cooper Meurer: Lately, I have been mulling the idea of selling my primary residence and renting for 1-2 years before we leave the Midland area and move to the Texas Hill Country (surrounding Austin area)Reasoning for this:- I currently have around 120k in equity in my residence and I have a 4.75% interest rate. 

Unfortunately, of everything that you have pointed out, this would be the one I would suggest selling. 

Especially if your son could then try to sell his primwry with the ADU under the sec 121 tax exemption I wonder if he could sell you the land?

Lets sell a dream or lifestyle.

Since they are considering renting their properties out, sell them on the concept of getting consistent cashflow from you - without the hassles of being a landlord.You will then need to make sure you can make those monthly payments EVERY month in addition to do remodels.

Then sell the property and start doing fix and flip or fix and rent. ( I prefer to sell this property as it 100km away from my student rentals. ) Not sure if I should renovate the lower unit to sell.

And I see all these people doing it with this scheme and that scheme, and real estate investing content seems a golden ticket. 

Unless you are SURE of $10-15k plus annual appreciation you sell. 

For example if the house is worth 400K, but they are willing to sell it for 375k because they are avoiding having to pay 25k in agent fees, then the bank can consider the equity gap as a down payment.

But inflation for sure with hot Austin market and ice storm displacements.I am also remodeling a Lake House in Belton, Texas that we will likely sell, but I really thought MTR might do really well.