Jason Hartman has pointed out that interest rates were so low before the recent increases, that buying was like going back in time and getting a mortgage in ~2011-2012.so... it still feels like the fragility of the current group of people who already own is a bit overstated.this is the distinction between the market being unaffordable (it's very unaffordable) and unsustainable (maybe it's unsustainable?)

Remember: Insurance companies want you to pay the bill and when it comes to their turn, will do everything they can to NOT pay.I would get clear on that piece before proceeding further.

The "home owner" is more like a tenant, in a binding contract to pay a rent for 30 years or cash to own that property, regardless of what is written on a piece of paper called Deed. 

No unit can be rented more than 2 consecutive years and so on.Another piece to consider is even if the bylaws today allow rentals... this can be changed at any point in the future.

Gues this is legal if they are sending monthly statements that an owner (or their tax professional) can piece together.Regarding mistakes, not aware of any company in the world that is perfect and doesn't make mistakes.

HOWEVER, Relay is only the front end/ tech piece.

You just have to learn the process and follow some  broad pieces of advice such as - don’t invest a lot in individual stocks because you are subject to much higher variances in performance.  

Ultimately the value of the single family home lot is the critical piece to the equation.With respect to financing the new build, assuming you receive the zoning relief and can subdivide the parcel and the parcel is released from the current mortgage you should be able to use the land towards your equity.

Another job (which doesn't seem DIY) estimate he's provided me is bringing out a stucco wall - this home is 100 years old and the wall is made of this:Outer most later stucco type of cement, wire mesh, plywood, 3 inch beam every 16 inches, thin wood pieces rubs horizontal with 1/5 gap and then stucco inside (this stucco grade is different from outside)The wall is just after the entry door to the right and if I open it up, I'll have a larger space to place a shoe cabinet and stool.

@Justin Reyes Let me ask you this...If you owned a marketable piece of real estate and no longer cared to own the property what would you rather do: (a) Sell the property, pay off your mortgage and move on to other opportunities; or(b) Sell the property without paying off the loan,  remain liable for the loan as the note signer and trust the buyer will continue to make payments on that loan, and if they don't your personal credit is damaged?