DSCR is not necessarily a better option in this case, they still need a solid collateral even more so as the building has to qualify more than you do. 

You will then have a few options with that rent money....you can put it into principal or you can start saving it to purchase yet another property.

I have lender financing options: 75% LTV, 30yr fixedA common strategy is what you wrote.

I have a few options:1) raise the rents without touching the property (cash flow could then be around 1,500$/month 2) update the units (estimated 50,000$) and then (cash flow around 3,000$/month)2) update the units and do medium term rentals (cash flow around 4,500-5,000$/month)I'm also having trouble kicking the current tenants out with how bad our housing situation is as well as homelessness.

You think they are going to create an option of "I'm stuck in my relationship and not filing for divorce cause financially we're screwed."

If you don't have access to the MLS, I've found that Prop Wire is very good for running comps since it has option filters that will make your search easier and faster.

I am just now beginning to look into financing options as well.

I have already contacted two other contractors for quotes in order to obtain three total quotes.I understand that some investors like to also make use of lower-cost options, such as neighborhood kids, but as I am running a business, I would like to maintain a process that is repeatable and predictable and that may also adapt to long-term needs, such as landscaping and weed maintenance.

As best I can I point out either evidence of issues if we can see them when we show homes, so you don't waste inspection and option money on homes you end up not really wanting to buy.   

In the future, a) get a super detailed Scope Of Work and ironclad Contract. b) Do not pay more money as a progress payment than the amount of work that has been performed, that way you are never ahead of the Contr or vice versa.Your options (depending on how much he owes you) are Small Claims Court, the State Registrar of Contrs, and possibly the local DAs office or State AG if the amount is higher ($50k ish)Good luck, let us know what happens.