However, in the off chance that I am not able to cover my gap funds (est. $200-$300K) from that small circle, how would you recommend I start branching out?

Or do they leverage debt, and use the subsidies to cover the equity needed?

Also note that my company will possibly either cover closing costs if we sell or provide property management for two years if we rent.

For best results shop the vendors (who can be covered by insurance/meet HOA requirements) and get several options to your HOA management company to have the board pick from.

I hope you have a lot of cash available to cover the FTC fines. 

The mortgage would be $5,200 so I would cover the other $3,200.

Lower property taxes, affordable housing compared to LA (CA buyers are usually cash buyers because what they net from their smaller home in CA can get them a bigger home here, often covered by what they net from their CA sale), allergies (smog), and politics. 

FYI I do have plenty of reserves for my other units already, but would like to keep each property separate.My question is, where should I draw funds from to pay the least amount in penalties, taxes, loan interest, etc. from the following sources I have available:- 20 year 401k loan for a property- Sell a piece of my stock portfolio at 15% capital gains tax- Take a HELOC against an existing property- Private money loan from a trusted partner I have worked with beforeAlternatively, I could pool the reserves for all my properties to ensure I can cover anything immediate and know that I could always sell off a piece of my stock portfolio if needed and have the funds within 3 business days or set up a HELOC and only draw from it if needed.Appreciate any thoughts or what you have done in the past.

If it is in a market where long term appreciation is expected, and conservative underwriting projects that the payment will likely be covered, then I think it is smart move. 

Do they like to be on the couch (if so I have couch covers)?