How would you approach learning the local market in the quickest and most sufficient way possible?

Have you had any issues with this approach or has it been pretty smooth sailing?

Option 2 seems like a more conservative approach but may take BRRRRing off the table so you will need to save longer to afford the down payment on the next property.If you haven't done it already I would run all of the contingencies through the BiggerPockets Calculators to see what will give you the best bang for your buck.I wouldn't get hung up on the fact you've never BRRRR'd, nobody has done it until they do it and plenty of people out there have proven that it is possible.

This so they can dismantle prop 13 in stages, the stealth based gradual erosion approach. 

This info might all be irrelevant but just thought I would share to get a better picture of approach strategy.

You'll need to find a closing attorney/company that is willing to do this - double closings are not uncommon, but depending on your state, your approach/strategy will need to adjust.  

When I first started out my approach was to consume as many podcasts as I could on the various niches of Real Estate Investing. 

As my portfolio expands, and I say “my” since my bf isn’t as interested in real estate as me and will stop investing after the first property, then I will be looking for trustworthy property managers to assist me with managing my buy and hold multi-family unit approach.

What would your approach be and could anyone help with the context of the letter i would mail?

I now have a lot of things going in which I pretty much don't know exactly what approach to take at the moment.