At first I didn't question the assessments.

First, as Tanner suggested, engage a general contractor to assess the property and provide a detailed rehab estimate.

Here are some diagrams to help you in your quest for answers on this subject:Asset Protection Decision Diagram - to help assess the need for asset protection, and what to implement : https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-decision-diagramAsset Protection Onion Diagram - what, when and at what cost one should implement in terms of asset protection - https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-onion-diagram-v2What is needed for a complete asset protection OR the domains that need to be intersected to find asset protection

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Another thing that can reach out and bite you in the butt is special assessments.  

As investors it is good to know and understand the skill sets one currently has and either develop or get help with those one doesn't have.  What skill sets and experiences have you drawn from?  When you look at diffe...

Our house is assessed at 415000 and the mortgage is 269000 and not declining because everything goes to interest, taxes, and insurance, nothing to principal.

(Most people know it by it’s slang name, “squatter’s rights.”)Under this scenario, if you claim the property for a certain number of years and pay the assessments against the property, (taxes etc) and maintain the property for that time.

I've been wary of jumping into the crowdfunding game, but I think I wanted to assess whether his approach had specific advantages that would prove more attractive.

Even if the HOA does cover things like windows, that doesn't mean they are currently funded to a level to handle replacing without a special assessment.