What is standard in Cincinnati Ohio may be a deal breaker in Chicago.The documentation is mostly in the public domain meaning that you can copy it and use it to make money without violating a copyright.

Have you talked to private lenders / hard money lenders?

Everyone has been scared the crazy state was never going to put a budget together and eventually the schools were going to have to shut down because they had no money coming in.So this may very well be a good time to buy as some landlords in college towns may have seen a decrease in vacancy and might be spooked. 

As for your question on the hard money lenders - I don't think it matters how you source the equity for a deal, but it's more important how much equity/downpayment you can put down on a deal - i.e. 10%, 20%, 30%, etc...

I'm not sure it's so straightforward to put a room in your primary residence into an LLC but at the same time worried about the risk exposure if I don't - any thoughts on the pros and cons of either would be appreciated!

How would you suggest I use this money to generate the maximum amount of monthly cashflow? 

They ask for upfront money something that I never done

I bought these properties cheap, had them fixed up and not have they appreciated a lot that also generate a nice tax free cash flow that goes back into my IRA to be redeployed into more properties.This is a huge tax free money maker. 

Money needs to be set aside for that maintenance.

Fast forward a year my sister calls me says she wants to sale the place makes no money.