I would like a payoff planner that helps me navigate the various maturity dates and interest rates of my (15 due in 5) mortgages so that I gain the best financial advantage when paying down principal balances. 

No but keep track of those repairs as it will add to your cost basis when you go to sell it and have to pay capital gains.

Quote from @Leeling Chew: It doesn't matter who pays the bills.

It starts with doing 10-20% of the work and paying much lower taxes.

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

I'd be looking at multiple structures. we try to build below the average new build cost in our market in Columbus Ohio which is 515,000 last year and we target land 40-50k and urban core adjacent where we get higher price per square foot. we build for clients with margin around $190 a sq ft depending on multi or single. we can get that down in our triplex it's a little higher on our single family homes because of garages and limited economies of scale. hope that helps. idk Philly but if you show me the area and styles of homes I can give you some more insights. 

If they work independently, set their schedule, and use their resources, they might qualify as a 1099 contractor, but misclassification risks IRS penalties.Wages for W-2 employees and payments to 1099 contractors are both deductible business expenses, but compliance is key.This post does not create a CPA-Client relationship.

My client's have been happy with the draw process and response times as well.

It seems that often when companies acquire large books of business in one shot there are growing pains and unfortunately those are felt at the client level.

@Andrew Slezak we're pretty aggressive about rent increases for our clients, but some of them won't approve us to pursue.So, don't automatically blame the PMC!