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.

Dilemma: Should I just buy a property (upto 450k) with 5 % down right now or just wait it out add both of our mortgage and by a bigger property up to 750k).

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. 

Our dilemma is what’s the best route to execute buying a second home right after we close on our primary residence?

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.

Out of all the videos I have watched, I don't think any of the gurus mentioned this dilemma so its not really something I planned for...