I'm sure most of them started with the same idea as you: work part-time until they are more financially stable and then jump in full-time.

Banks/credit unions/“portfolio lenders” will usually require loan applications, financial history docs, other various paperwork before being approved and most take a bit longer to close.

(House-hack)The main reason I'm getting into real estate is not only financial freedom for myself but to get my parents retired.

I don't exactly follow what you mean by "where we are in the cycle," but assuming you mean that RE is at or near it's peak in value, that would not influence my decision, especially if I could pay it off within a couple years with my W2 income.

Make sure there is financial incentive for the contractor to complete the job and get the last draw.

I work in the financial markets and have always had a passion for real estate. 

My ultimate goal is to have side income through rental properties and to eventually reach financial independence.

But as reality sets in, I probably can't swing both financially at the same time. 

Most importantly I would try to get financial info from the association and make sure they are well managed and ask about special assessments above the HOA fees.

It is good to understand and decide where on the spectrum you want to operate, but it won't influence your analysis very much.https://www.biggerpockets.com/blogs/4445/36354-041...