I think your wise to install a new roof, you can take the cost off your taxes and it will only add value to selling price, and it gives the buyer the peace of mind that they won't have to worry about a huge ticket item and shows your maintaining the property..Water  heater,, is a no brainier..

Below contains a few items that stuck out to me.Financing - Getting 1000 mortgages is impossible.  

Well, the main item noted is higher cash flow but that's a fallacy.Regarding risk, there are many ways to maintain higher leverage without significant risk.  

I'm not saying don't plan on spending nothing while you are living there, but that those line items for vacancy, repairs and capex are safeguards.

That includes rent increases above the allowable amount if the tenant agrees.The LTB requires that either Cap expenses are made, you provide a new service, facility , privilege or thing (item) to increase above allowable but that only matters in the case you impose the increase and the tenant fights.

My credit card no interest period will expire in June, so I need to start unloading those items. 

Working a Part-Time Job/Receiving W-2.And I Have Conservatively Purchased/Invested Roughly 10K+ in  Business related Items In 2016.

Here are some items I would ask you to consider:don't just purchase all your single-family residences on a buy and hold program.

I know its American & some items will be different, but its gotta be fairly similar.Are you using the BP rental calculator or something different?

I have used this attorney for a few years for several small simple items including drafting the leases that I curently use.