Originally posted by @Max Petrov:@Nick B.For me it takes much more longer) You  need to develop a model of a good deal and then just compare what you see with that model.E.g., your good deal may be priced at $80/sqft "all-in" in the submarket where retail houses are priced at $110/sqft and rents are above $1/sqft.You need to know these numbers before looking at individual properties.

Are you buying in Chattanooga proper or finding your deals in the smaller towns outside the city?

Looks like you are on the proper path. 17% discount from listing price is a bit tough. 

What brought my rents down there for a couple years is there was a ton of new developments in the area (yes development can negatively affect your property) and with the increased housing supply and new apartment buildings that went up, it pushed my renta down in that area.

So what happened in the end - it was insured properly I assume?

If any are late, hit them with the proper notices and evict or get them back on track.

So I consider myself a beginner.I have an opportunity where an old friend of the family, in his late 80s, had started to develop a 9 lot subdivision.

I called the Land Bank to see if I could redeem the property but it has already been sold to a developer. 

It is a large scale duplex project by developer with around 40 duplexes in community.  

You also may get tripped up by other things like proper support in the structure, ratio of windows to the buildings envelope (I'm not as familiar about this but have heard stories), etc.For some properties this added cost and hassle may be worth the investment to change the use from residential to hotel.