if you permit everything, and are good at the work, you should be fine.  

I charge $300 extra desposit and $15 more per month per pet.

We can put down about $100K and have extra cushion for renovations/closing costs.In your experience, if you were advising two newbies, would you WAIT to buy in Oakland until prices drop?

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@Paul Roman There is no magic wand to make an extra $200/mo appear.  

If those don't work, check to see who is pulling permits in your town as that is typically a sign of legitimacy if they go to the trouble of doing it right.    

You will need some drawings for permitting. 

With this being our primary residence and with all the other factors mentioned above, would you say it is ok to pay the extra $10,000 and not complete all of the finishes we would like to put in the home since some of them would only be cosmetic.

*combined with theirs an extra building lot would be created *Our house..which is an antique cape completely rebuilt after a fire.* It would make their land into a more cohesive piece.The access that they currently have is challenging..it would cost a great deal to get water and electric that far ( if they even want to do that).

A deck properly constructed is tied into the house, needs a permit, and  should be according to code.