I assume I use the current value of the property (I know its the value of the house only; excluding land) when I "convert". 

Namely, you must be able to show that all of the following are true:you are married and file a joint return for the yeareither you or your spouse meets the ownership testboth you and your spouse meet the use test, andduring the 2-year period ending on the date of the sale, neither you or your spouse excluded gain from the sale of another home.If either spouse does not satisfy all these requirements, the exclusion is figured separately for each spouse as if they were not married.

Your tax advisor is spot on—writing off a luxury car for your short-term rental (STR) demands solid proof of business usage; slapping a logo on the side won't cut it.The IRS lays down strict guidelines: the car must be regularly and exclusively used for business, excluding occasional STR trips or grocery runs.

At this point I am leaning towards just going with how they have been prepped (Sch E), although I don't want to set a precedent that excludes me from utilizing Sch C next year if it so happens that would be appropriate.

Payments that you make normally fall into one of 3 buckets100% of the payment can be factored in somewhere on the returnPartial payment can be factored somewhere on the return0% of the payment can be factored in somewhere on the returnHouse-hacking also has considerable tax implications in the event that you want to sell this property.You can potentially defer a portion or all of the gain on the investment property with 1031 exclusion.You can potentially exclude a portion or all of the gain on the personal residence with section 121 exclusion.

- assuming 500hrs each, we have spent enough time this year to get to that but wondering if thats a red flag for IRS with high chance of getting audited (we travelled 7 times over the past year to work on the unit and spend at least a week each time excluding the time we spent managing the guests)- Lastly, our understanding is that each can take 50% of the final offset to our W2 assuming we prove material participation eligibility. 

Hey Justin, Section 121 allows you to exclude 250k from gains as single and 500k from gains as married. 

Simply own and live in the home for 24 months of the past 5 years from the date of sale, and receive a tax benefit of up to 250k of excludable capital gains from tax or 500k if married and filing jointly. 

I was advised that the depreciation taken during the years it was rented is not excluded from the exemption. 

be mindful that those involved in the military are provided an 'extender' on their section 121 exclusion eligibility.Depending on the appreciation on the property(if there was), you may want to consider taking advantage of section 121 as the excluded gain may be higher than the potential cash-flow that you can get on a property.