There are multi-million dollar houses that you can walk just a couple short blocks and watch the neighborhood get pretty rough and potentially dangerous.

Hey Caleb, There are a couple local REIA groups that would be good sources to come network with local investors.

In a dream world - the comprehensive solution does all this: *task management and sequencing where you can drop a property into a sequence ie day 1 call, day 2 mailer (have it automatically mail out something like a postcard) day 3 etc etc etc*project management outside of the outreach sequences for what's next in the process ie schedule inspection, send the contract, etc etc*ability to have multiple users drive around and if you see a property you can tag an address and add it into a marketing sequence, and also track the streets you've hit so you're not wasting time driving by the same houses more than once *dialer (ability to parallel dial numerous numbers simultaneously to make cold calling more efficient - Ive used tools like orum and kixie in other industries, and when you receive a pickup, the other calls are dropped) *skip tracing/data provider *website landing page for converting online visitors to leads*electronic signature/docusign*secondary branded landing site on different URL for blasts for deal disposition to your buyer listWhat am I missing? 

If you spend a couple years of cashflow on a new roof, that means you should be free and clear for a couple decades.

That'll come out in a couple of weeks.

If you spread the 300k across a couple of assets, you will do better long-term, but worse short-term.

I invest in Detroit as well, and it's a city full of opportunities if you take the time to understand it.A couple of quick tips: Get familiar with the neighborhoods—Detroit is very block-by-block, and the difference in property conditions or tenant quality can be drastic just a few streets apart.

And I chose to buy the quad out for a couple of reasons 1. 

You are correct about that, but that's usually a computation and decision that an investor makes after a couple single-family homes or small multis.

I know a couple local hard/private money lenders I can connect you with, one of them is a sponsor at the Dover real estate investor meetup that takes place the 2nd Monday of each month at Chapel and Main Brewery.