It paid off very nicely & the majority became rentals or were eventually sold to buy more.

If you don't tell him all the reasons you got a screaming deal, then he must assume it was an arms length open market transaction, which in turn will mean the other home appraises low, which may mean it sells for less, which in turn means one of YOUR comps sold for less, which could impact market value of your home should you go to sell or refinance it.I would be selective about what I would share, and I wouldn't lie, but I'd only share information that will, or could, lead to my property selling or appraising for more. 

Based on comps in the area, it's about half the price it should be - however sale history shows it's about 40k under what it should be (previously sold for 200k, now at 165k).

Get the price per square foot of similar sized lots that SOLD in the area.

There are many, many properties that are in tired or rough shape that are being sold to owner occupants with little room (in terms of resale value) for spending money on rehabbing. 

Justin,Try Patty TaylorAll Insurance FloridaI sent her contact information in a Private Message. 

My brother and I sold a rental property for$345,000 in August 10.

Sold 7/19/18 for $250,000. 1794 sf, 3/2, built 1915, two story. ($139/sf).Comp 2 = 900 S.

Can you just purchase it traditionally with a bank loan or perhaps a private loan to get a higher LTV?

I would look at photos of sold condos in your area....ones that sold for top dollar and ones that sold at a discount.