I also think there may be some value in creative solutions for undesirable lots / houses that are not maximimizing their zoning potential / building higher end properties / or getting a head start in an under appreciated neighborhood. 

Holding costs is one thing but if you are making 80k or more a year you really need to evaluate if you 1) like doing this rehab stuff or 2) you should just pay a few thousand more for retail and save yourself the risk and headaches and get back to your w2 jobs and pound stuff out there.

Would focus on the following:Zoning, special/conditional use variance process, planned zoning, Engineering- building, traffic, soil compaction, water flow, Permitting, fire suppression, fire hydrants, storm pounds, storm sewers, ADA,     Governmental- soil erosion, floodplain, wetlands,Leasing, NNN, CAM,     Valuation approaches.  

It is often unsettling to spend that kind of money for a room that is obviously very 1965 on the inside with paint slapped on it and some vinyl flooring, and the furniture looks like an episode of Saved By the BellWhat's even more annoying is how they have their staff come pounding on the door at 9am when check out ain't for 2 hrs and you're trying to get that last hr of sleep in.  

Property was worth another 100,000 pounds a few years later.

NO....while I prefer to live entirely debt-free, I can see where investing in education *might* be "good debt", and also where if someone went into debt due to major medical bills, that would also be undesirable, but better than being sick...or worse.

Attempting to do it on your own would be penny smart & pound foolish.

They have 2 kids a 4 and 5 year old and a 5 pound dog.  

It's penny wise pound foolish.

Or, could this turn out to be penny wise, pound foolish?