-Over $20k in water damages from a broken toilet that they proposed to fix when it was cheaper just to replace.

Here is what I’m concerned about, i did all the work myself/ paid cash to get it done.Here are the upgrades(I’m sure some of these might not need a permit but I’m new So idk)-Added central heating and air -tore down two walls to make an open living concept (non load bearing)-renovated kitchen/moved gas line-replaced some of the foundation 2x6 floods became they where damaged by termites -add/move electrical sockets-new floating floor-replace pluming with pex/ pbc-painted inside-replaced a window- maybe more but you get the big picture.Will the appraiser report me to the city?

You input your estimated cost of replacement.

@Brent Smith Those numbers are fine as long as the roof was recently replaced and HVAC has been maintained.

The house could use new siding on two sides and eventually will need carpet replaced, so I may hold on to it to recover those costs.

It is very durable, sections are easily replace, and readily affordable.Generally the thicker you get, the more expensive, but also the quieter and likely more durable.Not sure why you would hire a handy man to do that.  

It's difficult to replace fear, but can you relate using other emotions, such as excitement of the possibilities for your children to learn from you?

If your newer home has a more modern layout or amenities, then that would increase value.

Are you planning one replacing that for the rest of his life?

Put in new roof, HVAC system, fixed, replaced parts, and refinished all of the hardwood floors, new kitchen. all of it, down to the non-existent 2 x 4s (historic fire in the kitchen, walls were cardboard and rolled paper in lots of places, new hickory cabinets, fixed falling in ceiling/roof for breakfast room, fixed foundation issues, new subfloor in living room, dining room, new stairs.