Should I pull the trigger and buy it, or wait for a better deal down the road?

The building permit may trigger the reassessment automagically, but you should ask the city specifically. 

I'm going to try (after I pull my first trigger, of course), to use it prudently.  

Hello BP Community,I have finally pulled the trigger on a long-time desire to enter the world of REI.  

Germain provides for a due on sale clause trigger for residential leases longer than 3 years.I'm not an attorney, but you may run risks of a tenant showing equitable interest in long-term leases that may make them harder to evict if challenged.If the tenant wants long-term security, look to commercial leases for renewal clauses and, like everyone's saying, keep the term shorter.

The hardest part is pulling the trigger on your first deal.

Setup a trigger for "motivated sellers" posts on Craigslist to send you an email notification when posted.

It's my first one and I'm afraid to pull the trigger.  

Once you have selected a partner that you trust to be transparent and have pulled the trigger on a property, there is virtually no work involved unless you want there to be.

But given that you have a 10 year time-horizon and a buy and hold mentality. don't be afraid to pull the trigger and fast!