I'd deduct this before accounting for your total cash flow. 

You could also do a cost seg on the $500K sale which depending on what the dirt is worth you can take a large deduction year one of renting it. 

For your $240K new-build townhouse, a cost seg may make sense if the tax savings outweigh the study cost (~$3K–$6K), especially since you plan to hold it for 10+ years and can benefit from immediate bonus depreciation.For the $380K older townhouse, cost seg with look-back depreciation could provide significant one-time deductions for missed depreciation over the past six years.

I THINK you could probably just expense your deductible if insurance didn’t cover 100%.

., electrical, plumbing).Project Timeline:Start Date: For the portion of work they are completing.Completion Date: Set realistic deadlines for their tasks, adjusted to your overall project schedule.Liquidated Damages:Specify a daily amount to be deducted from their final payment if they fail to meet deadlines (with exceptions for factors beyond their control, like severe weather).

You only want to file a claim if it's much greater than deductible or your rates shoot up pretty quickly. 

So, if your property has all bills paid by the tenant, you will deduct from the voucher amount the set amount by bedroom count for items like water, electric, gas, etc.

I would look at their policies and make sure both the coverage and deductibles meet your needs. 

Having the books properly set up for the first time ever will help me get all the deductions I’m entitled to.

And, factor in the depreciation and other tax benefits, deductions, home office, vehicle expenses, etc.