@Danielle Cage your realtor will be able to give you a lease from the local MLS that will be ideal for Kane County.

Ideally these properties will have positive cash flow + buy and hold potential (probably goes without saying). 

Aside from that you roughly know am I dealing with the top 25%, top middle, bottom middle or bottom 25%.

You're not looking to replace your job and make really good money, plus you live in an area that isn't ideal for buying locally.

Ideally I’d love to find a lender who would lend based on ARV instead of LTC.

That would be the ideal software but don't think it exists.Thinking in the future if I wanted to scale and buy more properties I'd like to have the ability to open more accounts for each property.Any input appreciated on the best way to set this up!

However, ideally if we started both with the understanding that collaborations and building the right team in conjunction for planning for our larger future and objectives we'd get to the "freedom" that we are all actually chasing via RE that much faster. 

The company I had just got sold and the new coverage is not ideal. 

Josh.. rentals are not ideal in a 401k  since you cant take any depreciation..

There may not be an ideal solution, but without knowing a little more it's hard to give advice.