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. 

Has anyone seen any issues like this?

As an individual, it is hard to open an efficient, responsible, profitable out of state network because as an individual you do not provide that much value for an agent or a contractor to run around and cater to you.But when you are part of a group that closed on over 4 million in real estate in six months and brought in over one million in local rehab dollars and put 50+ people to work and paid the city inspection office for all the permits, inspections, and reports then people cater you to. 

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?

  :)Financing for FHA and VA  will evolve to address their issues. 

remember your first home is not your forever home, it's your first rental so it doesn't need to be everything you want.look for homes where the bones are good, but cosmetically needs love. don't by pre 1960 if you can help it. you'll end up just having to replace all the guts like plumbing and electrical at some point. it's inevitable. look in areas where the path of growth is headed, but might not be currently. think 5 years out. look for resources like your local chamber of commerce to see what businesses are coming in and where. your city planning office should also be on your call list as they can help show where most permits are being pulled for development. follow the money. go to local investing meetups. crowdsource local knowledge and form meaningful relationships. those who've gone before you typically will help out and help you avoid the mistakes they've already made. onward.

Hi Matthew, Remember, navigating legal issues with tenants can be complex, so it's crucial to proceed cautiously and seek professional legal advice when necessary.

While the IRS allows this, it is a taxable issue.

I assume you have the foundation permit/plan and can provide that to them to bid, so you just need to send it over and have them provide SOW and pricing.