Sounds like your timing was fairly perfect (considering the spike and current lack of inventory). 

@Ray Hayward, there is too much information we lack about this situation, and about what you are trying to do and why. 

The lack of contractors and good contractors at that, the lack of places to get material, the holding time, etc.

I'm curious to know what you do with your dead leads? How often (or percentage) of your leads turn out to be dead?
Mainly, how often do you throw out your leads because there isnt enough equity in the house to make a...

This means the less cash you spend to buy the property, the less you have at risk.Based on your complete statement above, the reason why you lost everything had more to do with your lack of knowledge on how to analyze properties, and all the mistakes you said you made along the way.After ten years, using a combination of reinvesting the cash flow (part of it) and exploiting the compounding effect, the REI that only paid $20k for the same properties the other REI paid $100k for, could have had 43 properties and $215k/year in cash flow. 

But I ran across an old friend that is looking to sell some property.A little backstory on the relationship with said friend...I met this individual at the Apple Store several years ago.

Bear in mind that many of the posters have faulty opinions themselves because they lack experience and knowledge, but that a few experienced folk also post there from time to time to try to help.Visit the RV/MH Hall of Fame (Elkhart, Indiana) and spend a day or more in their library reading from their extensive works of now defunct publications and older books.

If you have a lack of comparable sales, then you should expect the appraisal to come back with a bad number. 

Are they lacking in a certain area that needs improvement?

From what you shared, it seams like your fiancé’s lack of support in real estate is only part of an overall problem with support.