Say they are rental cabins that aren't sold for a while.

I am a firm believer that reserves aren't simply a calculation of 3 months or 6 months of PITI.  

Bottom line if you aren't experienced enough to know all the ins and outs put an inspection contingency in there. 99% of offers will have it.

Sounds like both you and the investors are trying to cut corners and probably aren't cut out for this business. 

We both have decent paying jobs but we also have three little kids that we support so we aren't able to save a great deal.

Taxes and liens aren't always disclosed. 

vanilla purchase transactions where you aren't exposing the transaction to any reliability risk because it's so simple a dead chihuahua could underwrite it.Just to add confusion to your life, your realtor referring you to someone like me will likely call the local-to-you-me a mortgage broker even though in reality it might be quite rare that the local-to-you-me brokers on REI deals.

This condo would only be a play on appreciation, I am personally looking for an investment as well, but it seems like the only areas that aren't war zones that cash flow at least something will be around Humboldt park (The nice part of it), Belmont Craigin and Belmont Gardens.

You aren't going to be harmed financially in either event (personal or IRS).

Since there aren't already enough options... you could also look into turn-key investing as a hands-off approach. turnkey-reviews.com provides a list of great turn-key providers.And of course, you can reach out to me with any questions as well.Happy investing!