Before the RE discussion came about, we had decided it would be a good idea to pay off all of our debt first (1 vehicle and primary residence mortgage) before getting into the RE game.I would like to ideally use cash to fund my first deal as a lot of the financing options (HML, PML, HELOC, HEL, etc.) seem pretty risky for a beginner.  

I would ideally love to get hand on some properties that require little cosmetic changes and flip it quickly - just the way u did. 

Not to discourage you (if I haven't already) but this would not be the ideal place from which to manage a first project remotely.  

Don't put more time into until they are ready.Build that last little bit of rapport by saying something along the lines of "I would like you to find the best deal possible and it sounds as though mine is not as ideal for your situation as some of the other offers you have received.

This is something I’m curious about because it is not ideal with every situation.

Between the expected appreciation, the surplus of foreign cash getting parked here, and the high insurance costs.....this isn't an ideal rental market.  

Paying for performance is ideal, so be willing to go through the work of setting up systems to track conversions - any firm worth their salt in this space will know how to do that for you.Also, similar to direct mail, search is a bit of a numbers game - the number of searches on any relevant keyword will be finite, so you'll need to be addressing an area large enough to justify the cost of implementation and management.Best of luck!

Once I've figured out my ideal location, I obsess over the market there.

Making the third floor unit legal would be ideal but my current plan of action is keeping it a 2 family by treating the third floor as part of the 2nd floor unit.

I'd rather not borrow a large sum of money from my parents on a first deal, but at the same time I recognize that money from them would be cheaper than money from just about anywhere else.So ideally, I'd like to use a portfolio lender for the bulk of the loan, and my father for a much smaller chunk.