My partner and I were shocked when we received our first "quarterly" bill as we only had a 10% maintenance allocation and this bill exceeded that by almost 3X, totaling to $1985 and that absolutely killed our cash flow for the first 3 months.

Obvious reasons for this is to deduct all expenses and not do a pro-rata allocation of expenses. 

I would lobby for expensing this if it was my return.Charles...I thought the concept of depreciation was to allocate expenses to the year they produce income and not to "exhaust" the use of the property.

You should add expense for capes, building / yard maint, + you have not accounted for vacancy or property mgmt - even if you self manage I would allocate 10% for property management That said could still looks like a go depending on financing.

If you don't have to sell it could drop to zero, as long as it is producing income after expenses and allocations that is all that really counts, for me anyway.  

I think Jon nailed it; And, the only thing to add is that your basis as a % of the sale price, then that percentage determines the % of principal that is allocated to the basis, the excess is a gain on the sale.

Even being able to afford it, that seems to me to be a poor resource allocation, not any different than personally living in a million dollar house or spending $1000 to eat out. 

And, because you have been depreciating, you know what your original depreciation basis was for the dwelling structure and how much of your purchase price was allocated to the land at the time of your purchase.  

As a side note, I did a research project on lotteries back when I was an undergraduate, and as it turned out most of the states simply eventually substituted regular expenditure for lottery money - in other words, all the benefits such as increased money for education et al were never realized since the states just used the money that had been allocated before the lottery to do tax cuts or spend on other projects. 

@Ryan Murdock check out this link on how to allocate money https://i.imgur.com/u0ocDRI.png As others have said it depends a lot on your current financial standing but also you have one chance to live your life so don't stay at home every weekend eating ramen in the corner, go out and have some fun!