Considering the high deductible on House B, I am only filing a claim for House A, and coming out of pocket for the cost of repairing or replacing the roof for House B. 

In that case, you can take out cash through a loan without triggering a taxable event, even if you use that cash as a down payment on another multifamily property.

Some highlights: I have 3 homes up on Platform and manage another 2 homes.

Tennessee’s no-state income tax policy can be a nice perk for long-term wealth building.Indianapolis Pros: Having real estate connections in Indy could give you a competitive advantage on deals, local market insights, and trusted contractors, which can be invaluable for a BRRRR strategy.Ultimately, your “competitive advantage” might be stronger where you already have boots on the ground. 

Do I consider it as an SFH and assess potential rental income based on SFH?

From there, depending on the process, we direct them to the next step.

I recommend that you learn the tax code and take ownership over your strategy.Not having some foundational knowledge and an opinion on how to approach taxes as a business owner is a huge mistake.In my experience, every single business owner who says "I just let my CPA worry about it and I focus on my business" is doing a suboptimal job at tax planning.They are likely missing out on 10s or hundreds of thousands in saved dollars every year.Stop making excuses and get to work.Just a few months of part-time learning about taxes will pay you for the rest of your career.

You may find that you can rent a much nicer condo compared to what you would pay on a mortgage for the same number.

Purchase price: $50,000 Sale price: $160,000 Contributors: Peter Vekselman Partner Driven and Archie Raglin bought this Pleasant Hill property on Benton St for $50,000.

So they can do a 1031 only on their portion.