I have learned that HOA's mainly exist to tell me what I cannot do with my property/investment rather that contributing any meaningful addition or benefit to my investment.

Not sure why everyone loves CAP rate...it's virtually worthless in your situation and there are more meaningful metrics you should consider before writing off any deal.

, putting the remainder of my cash into index funds for the next 2 years, saving as much as possible, and trying to prepare myself to make more meaningful investment moves when my work situation is more stable.  

You have to consistently follow up in a meaningful way and you will get deals.

I want to do things the right way, have fun, and build meaningful connections with everyone that I meet.

@Rene Doyle a cursory look at wiki shows stagnant population since the 80s, 70k people which is quite small for the msa, no meaningful job growth, 3 primary employers in 2 segments, and a median income in the 30k range which suggests rents no more than 750mo. not favorable my standards but that doesn't mean there aren't good deals. a remote investor will have issues typically finding a great team in small tertiary markets like this. if you have inside knowledge that it's about to pop with a big employer then perhaps.

Achieving the extraordinary is not a linear process, the secret is to put in the time every single day on meaningful tasks and to work through the many frustrating aspects of the journey. 

You have to consistently follow up in a meaningful way and you will get deals.

Not illegal and definitely possible. however, some underwriters may question motives if they see you doing it frequently or are not making meaningful changes.

However, you then say that over the past 2 years, the SFH has appreciated by an additional $65k (either due to your remodeling or general market appreciation or both).If you hold on to this investment, you really are passing up the opportunity to extract $100k (omitting transaction costs and income tax due for simplicity).