In normal times i would think selling is typically the smarter financial choice, but at the current time keeping may have a significant finance (due to low interest rate) advantage.Here is a list of why adding ADUs in my CA market is typically a poor RE investment:1) The value added by the ADU addition is often significantly less than the cost of adding the ADU.

Make sure to also include in your calculation all the associated costs of those homes (maintenance, cap-x, management, vacancy, etc) then include the selling cost of the home since the appreciation isn't unlocked until you sell the home.

Gradually raising rents, exploring lease buyouts, or selling with tenants in place are balanced alternatives.

When I buy a property it is usually from someone who Really, Really needs to sell.

Or you have off-market deals you want to sell to them?

This may affect value or time required to sell.7) Adding an ADU does not make the property a duplex.

Hey Lenny,Love to see that you also got the Real Estate bug so youngI recommend a BRRRR/house-hack for your first oneBuy a place that you can live in with a low downpayment, fix it up, and then you will have the option to 1) Refinance and live in it2) Refinance and rent it out3) Sell and do it over again4) Dont refinance and continue to live in it5) Dont refinance and rent it outYou will have a ton of flexibility and the safety of knowing you have a place to livePlease reach out via DM if you have any questions moving forward.

Your wife as conservator/guardian has an obligation to her mother and selling the property to herself creates a conflict of interest in that she stands to benefit as the buyer and is also making decisions for someone else as the seller.2.

The owner has taken it off market and I'm just trying to explore my options of selling it off market for a deeply discounted price.  

It's hard to harvest equity on these plays, unless you commit, long-term, towards very light leverage, as the only practical ways to benefit from the equity in your portfolio, if you plan to never sell it, only exchange it, for a lifetime, are to spend the cash flow, or cash out refi.