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.

as long as your not paying any fee's up front other than appraisal and maybe credit report ... sounds fine.. no way a lender can stay in business if they do not capture at least 5k per file no matter the size.fee's and points do not go lower exponentially as the loan amounts drop.so if your payint 12.5 on a 40k loan or 5k... your not going to pay 12.5% or 50k on a 400k loan like Jeff alluded to.. there is simply a minimum to stay in business

I hope your REI investing is going well so far in 2017 and if not I'd be glad to discuss with you how you can improve your game.I have a question however regarding a system for capturing all my incoming leads.

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.