When one of these properties does surface, rehabbers snap them up at a premium and then must go to the retail market to profit.

Who owns below the land surface?

If others in the area all have new windows, hardwoods, and solid surface counters then you need to do the same.What are the numbers, comps and asking price?

My first modest repair issues should likely surface in about 5 years, at which point I should have a nice chunk saved up from the "maintenance fund".

Except, I always just wanted (loosely put, wanted just touches the surface) to spend my life redoing ugly old houses.

However on the surface it certainly would appear that way.I'm certain that you spend a large sum of money each year advertising to attract customers to your agency and I congratulate you on the job you did as I was initially attracted to your agency.

(Very expensive) usually you can mitigate most water penetration issues by simply addressing drainage at the surface.

On the surface the deal looks good and the seller said there might be grants available up to 350k...???

But, it does show wear patterns in the surface.

@Kevin Seith Tear downs are more costly as mentioned by @John Moore there are usually additional costs for permits and engineering and you can't forget having to comply with all the current zoning rules like setbacks, off street parking, sprinkler systems, fire separation, density, lot coverage, and impervious surfaces.