If the current year water will is not paid within the year, nearing the end of the year(around late Oct/early Nov) the water works "rolls" the outstanding water bill into the current years taxes. 

Also, if you have tenants in place, you'll have to wait until your leases roll over to implement this charge; however, I would think you'd have to do the same if you sub-metered and wanted them to start paying for their own water.

We are going to roll out a powerful vacation rental website in about 2 months.

You could roll up a entity, and write off the office supplies or whatever you want to catalog it as, but the write off value on them books will likely be worth less than the cost to form the entity, documents, and tax filing cost.Once you have a working business, you can absolutely write off software, books, seminars, guru program, etc..

Do your homework on the all the possible expenses and ways the property might go over budget, which roll into #33: Where to get the money for the fix up?

I agree, you could roll over the 401k and take a loan against it for your down payment. 

I'm mainly interested in the rent roll.

And, as noted, a circular saw with a clamp guide (plus sawhorses) is truly your best bet for sheet goods.That said, I built a roll-around storage table with locking casters the same height as the table saw to use as an outfeed support.

Rolling fast, hard, and blind.

Rates today are historically low and I think I'd rather have a guaranteed rate than roll the dice in 15/20 years when we want to refinance and have no clue where rates will be.