- What do I need to ask for contract wise?

If your place is roughly similar in size (sleeping wise) then renting it as one place is the way to go.

I would recommend asking around for who people use as a property manager in Indianapolis so they maybe able to give you advice and help you make wise purchasing decisions.Finally, start slow and learn. 

But offsetting your cost of living by having roommates pay most of your mortgage and capitalizing on Boulder's consistent appreciation makes it a wise move for those that can pull it off.

Also seemed a bit hard for number wise

Unless you have money to gamble - Wise choice! 

When are lenders more likely to offer LTV loans, market wise, and based on me the individual?

Would it be wise to accept this offer if everything else checks off in their applications?

Having a bunch of active partners versus a syndicate can be a mess as voting rights and infighting on what to do with a property if something goes awry.So when I do anything transacting or syndicate wise I ask (Is the juice worth the squeeze?)    

Not only was that a wise financial decision, but it allowed us to get a primary house (which has since been Section 121'd) AND our first rental.