I said that I wouldn't do this deal if I weren't covered as far as either his mistakes, market timing, other myriad things that could go wrong; he seemed to think this could be overcome.Is he crazy to say this can be overcome to protect me?

San Diego historical appreciation can overcome small RE investment mistakes. 

The answer becomes more SFRs, but this can instead of solving the issue, exacerbate it, leading to so-so communication.Thus, I think that most TK guys and gals are good people who try, but there are structural deficiencies that are almost impossible to overcome within the model itself.As you know, when we buy apartments, property management, contractor budgets, and pay roll are all included into the model.

Perhaps your otherwise organized approach would suffice to overcome the issue.

But if it didn’t have the services and infrastructure surrounding it that could feed it with tenants and that’s why the previous owner failed, that’s harder to overcome.

Thanks for all your responses helps one feel better to know others have overcome the fear.

I understand that your wife may be worried about failure, but any kind of investment comes with a chance of failure so the risks must be understood prior to jumping in and the fear must be overcome with the confidence of being successful.Since you're starting funds are $0, a HELOC can be a great tool for getting started, but ultimately you will need some kind of funds of your own because you must pay the HELOC each month during the flip.

When you were ready to purchase your 2nd, 3rd and so forth properties, what financial hurdles did you face and how were you able to overcome them?

Good locationsAdd valueCash flowLong term debtReservesA good recipe with any market conditions.See below for a post on overcoming fear of the market.https://www.biggerpockets.com/forums/311/topics/59...

It's 100% do-able to buy sight-unseen, despite what some folks might say (you'll have to put in more work to overcome the lack of personal market knowledge though).Why?