This front-loading of deductions can be advantageous for reallocating funds, but it may affect long-term tax strategies.

I've always been curious as to how the sub to purchaser deducts the interest portion of the mortgage payment from their taxes since they don't have any legal obligation to pay?

The problem is, I don't want to take the $25k deduction.

However, based on our conversation, this strategy might unnecessarily complicate things.As a 1099 contractor, can I deduct all upfront expenses for the STR upgrade, as I did with my San Diego property?

One with 90+ members is great because it affords the HOA a lot of economies of scale with vendors thereby keeping HOA fees lower.Review the HOA financials and make sure they have a substantial reserve that would cover a hail storm deductible and/or other storm damage.Read the Bylaws to make sure they're rentable and check the pet limitations.Check the common grounds for any big ticket items that may need replaced soon.

If they file separately then only she can take the exclusion deduction on sale up to that 250k cap(since she did live in the home 24 months out of the past 5 years), and he cannot (in general). 

Quote from @Julia France: I am new to the concept of bonus depreciation and trying to get a better understanding.Some of your questions are answered in this long post: https://www.biggerpockets.com/forums/51/topics/1121063-expla...And then there's an STR-specific issue of what people like to call "STR loophole"https://www.biggerpockets.com/forums/51/topics/1122635-the-s...Other questions, specifically timing of your deductions, are case by case.

As a landlord, I do have to set aside a quite substantial reserve amount for capital expenditures, and it would be great if there is a way to have those funds counted as a deductible expense. 

As such, payments that you make need to be prorated between business deductions and personal deductions.

I was wondering if there are any deductions that I can take against my W-2 income, or if all deductions can only be taken against the rental property income?