Along the way to pay for our health insurance (partner and self) which had crept up to $1400 a month pre-Obamacare I took on a W-2.

Waiting & saving more for down payment leaves me stuck renting my personal residence and potentially can't keep pace with market pricesI'm considering putting my rental purchase on hold and buying a personal residence first to secure my financial health but this still leaves me at square 1 with my investing journey.

Yeah they'll write the listing (probably poorly) and hire the photographer, but as far as I know they're not going to order a couch and assemble a dining table and stock the kitchen and all that jazz so you've gotta do that either way.FWIW if you're really intent in not traveling to set it up, I did hire someone to do that part for me in one of my properties where some family health issues came up and I really couldn't get away for a week. 

Is there any regulation for an actual health concern?

However, nonqualified use does not include any period of such use that occurs (1) any time during the five-year period ending on the date of the sale that occurs after the last day of use as a principal residence, or (2) any time (up to two years) that the taxpayer is temporarily absent due to a change in place of employment, health, or unforeseen circumstances. 

Owner is an aged widower man in failing health that NEEDS to move to a nursing home or assisted living facility. 

We all insure our health, auto, homes from fire and theft - most want to avoid paying for flooding coverage.

At least one of us should be able to continue working remotely (how do others get health insurance without working a normal job?)

These tips can also be used to achieve success in other areas of your life such as health, relationships, etc.1  Positive Mental AttitudeThe only thing in life you have control over is your mind.

My vision is larger than my fund, and revolves around ensuring that those who live in marginalized communities have access to the social determinents of health (education, economic opportunity, healthcare, and homes) and are able to get themselves on a pathway to generational wealth through home ownership.