Being licensed means taking on a legal duty that limits one's ability to take certain actions other investors can take.I know people who became licensed stock brokers but never got a job in the industry.

Notable examples of folks being burned buying company stock at a discount include, but limited to, Enron, Worldcom, Lehman Brothers, GM and a whole host of other companies.Having worked in finance for a long time, I can tell you that no company is doing you a favor by letting you buy their stock (discounted or otherwise).

When you do, the sky is the limit.

Above you mentioned that coverage on the dwellings wasn't that important so if you wanted to keep cost down you could use the more basic DF1 policy (ask the agent down there) and market value for the dwelling coverage amount with a higher deductible and then max liability limits (probably $1 million). 

Your mostly conventional approach is limiting you. 

So what do I do - especially with limited cash for now??

@NhiQuann Jones from my limited knowledge, if you have a property that is paid for in all cash, say $50k... and you put in $30k of renovations... and that property appraises for $100k... you own a $100k property outright.  

I want to avoid personal guarantees and limit my cash outlay as MUCH as possible.

It really depends on how much equity you have in your primary residence.You could also use the HELOC for down payment and cash reserves for any rehab or maintenance needed.Then once the property is stable you can cash out refinance to pay your HELOC back and replenish reserves.With the limited information provided this would be my suggestion.

However, I live in an expensive market (NYC) and so will likely have to be limited to buying an investment property out  of state so that it can cash flow.