I replaced this out of my pocket. 

What I did:Painted walls and ceilings with sherwin williams superpaint dover white.Trim and kitchen wainscoting was painted with super paint semi gloss white.Ripped out plaster tub surround and replaced with cement board that was waterproofed and tiled.Replaced some missing shingles on garage roof.Replaced old shower valve with single handle valve.Replaced garbage disposal.Replaced old outlets/switches with new white outlets/switches/plate covers.Jacked up sagging portion of house and sistered three of the joists and replaced the rotted sill plate.Removed vinyl tile from laundry floor and painted the concrete with grey floor paint.Before photos:  Apologies if they are sideways or upside down...The after photos can be seen on my zillow ad, https://www.zillow.com/homes/17439-cicotte_rb/88664724_zpid/?

I guess I'm just considering all the hidden things that would need to be fixed or replaced that I can’t see.

It's an even more toxic charge than a security deposit, replacing "don't expect this money back" with "there is contractially  no chance you will see this money again." 

Many may not consider boilers to be obsolete, but we do & replace boilers the first chance we get with Force/Air cooling for each unit. 

Also, I feel confident that I can pull this off and keep my design job until I can replace my income.

The problem with this is the material costs can vary and you would need to determine if you would use the cost of material that is similar or exact replacements. 

----------------------------Replacing them with . . .  

Obviously, I want the tenant to be happy with her stove but I'm also bummed out about replacing an otherwise well functioning (and beautiful) stove. 

I knew instantly that we were going to need to replace every stud in the home and basically start from scratch.