The more you can show that you have community support (talk to your neighbors of the property & the local biz) and potentially MEDC conceptual support that will go a long way. 

buying 1-2 rentals that break even/have a little cash flow would be my choice given that I'm able to save 100k a year and potentially have cash flow from my rentals, means I'd still be able to pay my mortgage on the primary and the rentals.

Right now the majority of viewing requests I am getting are from potential tenants that have credit issues and eviction filings.   

(Yes, there is a potential Section 179 alternative, but it is for a different post.)  

This is especially important when owning rental properties or managing flips because it minimizes your personal liability.However, many people stop at forming an LLC without considering the potential tax benefits of electing S-Corp status.

There are potentially 100% loans like VA foreclosures, and also depending on where you buy. 

Hi @Tim Holt I think in general house hacking is usually a good move because it gets you off the sidelines and into the game with the most favorable financing possible (30 year fixed).There's a lot of value in getting started today vs waiting some undefined number of years until conditions are better, which could be a long time from now, because real estate is a business and the sooner you start actually learning about that business, the better.With all that said, I always recommend that people analyze any potential house hack as a pure investment that they aren't going to live in, because someday they may want to move out and you should know up front (before you commit) whether you're going to be able to do that, or whether you're overpaying and will be stuck in the property unable to move out because it'll be cash flow negative if you do.So you had it exactly right when you wrote, "the property would need to cash flow when I move out and rent out all units."

Quote from @Levi Perl: Hi,Curious if anyone has what to say in terms of how to calculate which one is more worth it: to cash out refi on a Long term rental now at 70% LTV, and walk away with X amount of positive cash AFTER paying all debt, (X is a positive number and significant amount for me), which will allow me to potential get another long term rental and grow portfolio faster, or wait 4 months and cash out 80% LTV, giving me DOUBLE than X. 

Maybe even failure to take full advantage of an opportunity, resulting in a loss of potential profit or benefit.

Growing at this breakneck pace, the startup could potentially rival AirBnB as a revolution in real estate.