If so, having cash flow negative assets or assets that one unforeseen expense wipes our years of cash flow is not an investment, it is a monthly bill like your cell phone or utilities.If you are banking on appreciation, that is a different game, and I would be looking at single family flips to get in and out quickly, but there are clearly a lot of risks associated with those as well.

On the other hand, I would agree with where Karl is headed, and that is that there may be some legit extenuating circumstance that has led to this unique position.

Several times a year I will get a deal where I spent 2-3 years following up with a seller before their circumstance warranted selling at my price.- the same follow up principles apply to direct mail as well.

Any unforeseen spending could end up with you leaving money in the property.

In very limited circumstances, the Act exempts owner-occupied buildings with no more than four units, single-family houses sold or rented by the owner without the use of an agent, and housing operated by religious organizations and private clubs that limit occupancy to members.Is it a SFH you rented without the use of an agent?

So far, on the properties I’ve analyzed house hacking may lower my monthly housing costs by ~200-400$/month (although I do realize this could quickly be negated by maintenance costs and unforeseen repairs); my train of thought is that I would still be contributing that 36k towards an asset that is building equity (while someone else also helps me achieve that), instead of paying it in rent with no return.

There will not be many unforeseen surprises as long as you buy a Condo in the right location and that has a well managed Association with a significant amount in reserves.  

Congratulations.No one can answer that question other than your CPA, because it is "case by case" i.e. dependent on the facts and circumstances. 

Under certain circumstances, you can expense property in the year of purchase rather than add it to your basis and depreciate it over a number of years.  

So far absolutely no issues with moisture and since there aren't chemicals being used in the water it helps overall maintenance with the pool pump and the interior of the pool room doesn't have as harsh of conditions/smell.Also, there will be things like self closing doors that are required (unless very unique circumstances which I could describe if necessary), pool alarms, etc, but that will be overseen by the local building inspector for the County, Chris Jenkins, and that'll have to be done or the builder won't get a CO.