Additionally I like to evaluate the financial health, capital reserves, and property condition of the association to try to understand whether a large assessment is looming.  

Cardinal Financial will fund out of state investors.

My goal is to eventually become financially independent to the point of being able to work my current job 6 months out of the year.

. $1.1 mil + equity in my property (no liens, and very good credit score)Since I am running a business on my first level of my home, I couldn’t find any financial institution to secure me a HELOC (apart from point.com which doesn’t seem a good deal for me)…apparently, the lenders don’t like mixed commercial/residential type of business (e.g. assisted living).

These will be my first two properties and it will give me a way in the industry, but I also don't want to make a bad financial decision.

A contractor is more likely to have financial issues when he doesnt get money up front .   

If it is true, you  or more likely the person living there that needs your care may be able to get some financial compensation.

More specifically, could it make financial sense when it comes to purchasing properties such as SFRs,Duplexes and Triplexes?

I have been exploring the topic of financial freedom for a long time, and though I haven't been able to realize that yet I believe it is possible for me. 

A lot of us (80%) who stumble upon simplepassivecashflow.com and start drinking Kool-Aide will be financially free in 4-7 years pending taking action.