Furthermore knowing rents, cost of money, minimum profits, how to work with appraisers on flip houses, etc. is a lot of work.Try this - find an agent that is investor focused and always have that friend to ask questions to, maybe related to contracts, comps, finishes etc.It sounds like you might be wanting to work with her because it is convenient, get out there and find someone you wont feel bad about firing.

I see too many condo deals like this in my area (Reno, NV) and keep passing because it looks like these wont cash flow.

Is chicago similar in detroit in that they suffered alot from the recession and will take a long time for it to recover?

At this point, the deal might be sweeter because I wont have to oversee the rehab and theoretically, Ill be able to finance the rehab into the cost of the loan easier.This deal won't work if it wasn't built on large amounts of trust.

But a while ago, I heard Dave Ramsey say that he "loves real estate but he wont go into debt for it".

Realistically you probably wont be able to get financed for two at a time if the lenders know you are trying to finance 2 at a time so one will likely turn you down.

Some wont even consider working with an investor who isn't incorporated.

Further, I dont anticipate I will get conventional financing for this in the near term anyway as I already live in my building and I checked and they wont finance a 2nd unit in the building due to higher risks of default etc.

It wont show up on your personal credit and it will give you some immediate cashflow so you can jump into another deal and recoup your losses.

I go that low when the tenant has a good history of paying at least that amount for rent previously AND that tenant has not suffered a decrease in income.