Taylor,I hope you aren't still dealing with this issue!

Each year by January 31, you or your bookkeeper has to total up how much you have paid to each person and issue each one a 1099, which is a simple statement of that total amount with your contact information as the payor. 

If we cant make money (for us, relatively early on please!)

I don’t see a huge issue with a 5-year term right now as most folks are planning to refi in 2-5 years at a lower rate anyway.

However, I have two types of clients that relate to this scenario: 1) The client who is over protective, and puts each one of their rental properties into its own LLC/Trust and 2) The client is who focused on simplicity, and puts all rental properties under the same umbrella.Neither one is right or wrong, it just depends on what is important to you.

@Joy Christina, Zillow, and other real estate-related platforms will likely give the property the greatest exposure to potential buyers.

Im a realtor here in Tulsa who specializes in investment properties and I would recommend visiting the OREC website by clicking the link below that will take you straight to the 'Residential Lease Contracts and Forms' tab. https://oklahoma.gov/orec/contract-forms-and-related-addenda...

I'm 26 yrs old and living in my parents house (3 bed, 2 bath, ~1300sq ft) in a relatively low cost area for NOVA (Woodbridge VA). 

Not sure about Indy market, but foundation issues are relatively common in 1800s homes.

3- To record incomes and expenses correctly for tax issues, do we need to make an official contract for the renovation (between the LLC and one of the owners), or is simply issuing invoices and receiving payments in the LLC’s bank account enough?