I think He needs to read Dave Ramsey, sell expensive cars/trucks, adopt a side hustle where he can deduct his vehicles, travel, health insurance, etc.

A lot of people skip this but it's a huge advantage if you can work through itEvery Landlord's Tax Deduction Guide- is a really good book on taxes and setting yourself up for success as a landlord

Ever since then, we've been contacted by multiple roofers who work the insurance angle (we can get you a deluxe roof for your deductible, etc.).Here's the thing: the roof is original from 1978 and was trashed long ago - shingles were already peeling, vines had wrecked havoc, gutters are falling off... this thing needs the works.

Deductible: This is not a coverage but rather your portion of a claim.

1031 exchange - do you know all the rules to follow to properly do a 1031 exchangeHELC - is the interest on this deductible?

Which Real Estate tax deductions apply to personal income, and which only work for income from the Real Estate itself?

Do you know if it's possible to deduct property-related expenses from a property in the Cayman Islands, similar to a US property?

Depreciation will arguably be your largest tax deduction related to your rental.

Otherwise it will get messy eventually.From a conversation with a banker, my impression is that their bank will either look at 75% of gross rent (when you don't have a 1 or 2 year rental history), or 100% of what you reported on schedule E (which is rent deducted all repairs and things).

If you can find one that cash flows as well or better than your last one, then you'll still earn that extra $1000 per month, but you'll have double the appreciation and loan paydown benefit and perhaps take another step closer to itemized deductions that save you on taxes as well.