I have done this multiple times and have had great success.

I have contacted them multiple times of course and a popular reason Sherman Bridge provides me is that the person in charge of my file is no longer working there.

Seems you have multiple incremental steps that can all be relatively easy and get you closer to your goals. 1) build an adu, 2) fill the adu, 3) buy a new owner occ, 4) rent out the existing, 5) look for another investment purchase (I suggest a great off market deal) 6) get it in escrow subject to selling existing investment property 7) sell existing 8) Use gains from selling #1 to buy #3 (which should be bigger and have more cash flow).

I am looking forward to engaging in some great discussions, learning a ton, and making some new friends in the business.

If the lead has multiple properties, there's no need to send them a letter for every property.

I've been reading the blogs, going through multiple podcast, purchased a few books, etc.  

Based on what I've observed, most rentals this close to university are inhabited by multiple people, many of them students.

I have insurance with multiple insurers, and my umbrella covers across the others so long as I have maxed out the liability with those insurers.

I'll definitely work towards engagement.  

You could make a much better return leveraging that 500k across multiple properties.