Both of which cause inflation while lower wealth people spend less causing a recession.  

Even if you have no plans to fill in the gulley, knowing if you're allowed to fill it in and what you are allowed to build there may help your cause. 

Holding the property will put me in a better financial position, because if I sell I have to reveal thins information that everyone mentioned, which may cause a bigger hit.

Then your lack of knowledge causes you to lose MORE money than the cost of a PMC.It's no different than life, house & car insurance - no one likes paying for them as you don't need them - until you do.

Short story is that after a "reset" about paying on time last month it's 5/19 and I have half the rent and just had to send a plumber out to address a tenant caused water issue and I'm done at this point.

I'd sit down and ask myself some questions, like how much capital am I willing to put into this endeavor, and I do not mean just one deal cause any deal can lose money. 

This requires an income that rises faster than inflation, or you will not have the additional dollars you will need to pay future inflated prices.What causes rents (and prices) to increase?

If you have to submit the written lease to the condo association two different names on one lease I doubt they will ask about relatedness but if you have two leases it may cause an issue.  

If you're providing an "up-scale" environment and hope to attract more guests of this calibre (I do; they don't quibble about higher nightly rates and rarely cause problems) then I recommend white duvet covers and wash them after each guest.  

My property taxes are high - around 9k a year.I’ve been out of touch with the market this year dealing with an illness and I’m trying to make the best decision cause this is my lifetime investment and extra income.