Given you have a disposed of asset, you would have a requirement to capitalize the new roof. 

Is he required to issue me a 1099 form for rental income for 2023 taxes?

I've worked with clients that have had to put more money up front into the transaction because the specific bank they wanted to work with required it.

General requirements would be 20% for a 1-4 unit property, DSCR of at least 1.00x or greater, and you can qualify with a score as low as 620.

Gain valuable insights into the intricate aspects of property management and develop the skills necessary to navigate the dynamic landscape of real estate management.Refinancing Strategies:Working with Lenders: Learn how to effectively approach lenders for refinancing, including understanding the documentation required and how to present your case in a compelling and persuasive manner.

First you cannot buy a Multi-family as a Vacation home its only for SFR - single family, condo's, townhomes and they require 10% down.

Also, thewholesalerstoolbox.com has a link to another affiliate that provides such info but requires a subscription. 

You are not only impacting your tax return but the tax return of your family members.Partnership returns became more complex recently with the requirement to keep track of tax basis for each member.

If your looking to house hack I recommend you research the VA habitability requirements.

Also if they won't give you required info find a other qualified tenant.