I haven't been very active nor very deliberate in our investing. 

The person who responded to this either doesn't understand lender's loan policies or is being deliberately misleading.

I deliberately did not mention the real estate investments, because numerous people had done so before (and now after me).That's what's so great about this forum, because there is so much expertise and experience (including yours).Yes, I do agree that a person with $250K needs to invest differently than someone with significantly more. 

After much deliberation, we decided to keep the existing foundation and exterior walls, and go up from there.Although I received advice from some folks much wiser than myself, to tear completely down and build new, we decided against it.Mainly because we have not done a new construction job yet, and we all really wanted the experience this one will give us before we embark on a new build.

I've learned over the past few months that time isn't the obstacle but deliberation was my road block.

@Robert Bartman Because you seem to be boasting about this deal, methinks @John Thedford is being deliberately provocative?...

I recently purchased a 3-family home and also deliberated this same question for a while and finally decided to go with the replacement cost of the house policy. 

I deliberated for some time about sharing the experience, and what I learned, and ultimately decided that if it was of some benefit to this amazing community, I ought to.A quick recapI partnered with a contractor on this deal who was referred to me by someone I really respect (an executive at a big RE company).

I hate the idea of not trying to rent earlier and deliberately going with a vacancy for at least a month.

That's deliberate damage and theft.Having said that, there's not much you can do that's cost effective.