How did you first start working with investors to allow you to raise ~$1-2M?

You claim to receive no remuneration for this from the syndicates you are pitching- but only time will tell if you're the only guy not getting paid to raise money for others.

I would like to think in a way that investment in general, and the real estate investment, start with a solid economic reason - "Why do you Invest, where you invested".To elaborate on below - Vegas is a great example where no real economic driver exists and when you invest there, you should be aware that is a highly volatile market (side note: i both 2 properties there in 2011 and 2012 and i sold both this year) and you should pay an extra attention and be prepare to reposition capital.It's clear, if you invest in Vegas or Orlando (just 2x entertainment cities) you will expect ups and downs and you need to position yourself with extra reserves and extra caution if you are planning to stay in these market for long term. 

New pictures, updated amenities etc can help raise your rankings.

As you seem to be aware, class C is risky.

I am aware that since I’m renting one unit out I need a landlord policy, but can my policy be HO3 or does it have to be DP1? 

I have lived there part-time and raised 2 children there.

With your balance sheet and cash, you can put together creative deals without giving up equity and without using your cash but you are going to need to find a market and product which has 7-8% cap rates.I invest in the northeast, Great Lakes area.Diverse economies with education, healthcare as the back bone and tech as growth.In your area, you’ll have to raise way more capital in the form of equity just to meet DSCR with the banks.

It's not just shorter-term downturns to be aware of, real estate just like the stock market can experience 10 year periods of no growth. https://fred.stlouisfed.org/series/csushpinsa

But that's the 50k-foot perspective.I am local to you in CT - Middletown born and raised!