I'm not quite ready to pull the trigger on investing just yet, but my primary residence is in Middlesex, and my husband and I are considering holding the property and renting it when we move on to something else in the next few years (we got an awesome deal when the market was still bottomed out and now have over $100k in equity when we only paid $200k for it).  

First, make sure a transfer to the LLC  wouldn't qualify as sale to the lender (it might trigger a due on sale clause.)

Keep the irons in the fire on both ends, that way you aren't coming out of left field when its time to pull the trigger.  

Obviously this is a very big decision for me and I just want to get all my ducks in a row making pulling the trigger.

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.