My question is, do I just use the heavily reduced price I was able to purchase it for since it was vacant, and then the material cost of what I renovated plus what things I did contract out, even though that basis would be way under what the other renovated houses that sold near me per SF sold at, or are you able to use similar comps to determine the depreciation basis?

We certainly have found some deals that would reduce our living expenses compared to renting.

The advantage if needed by calling it an investment home is that you can use the potential income from the property to help your debt to income ratio where you cannot do this on a second home. 

On the other hand, a detailed quote with a higher total may offer more transparency and reduce the risk of surprises as the project progresses.I specialize in consulting services for situations like this, where I help clients evaluate contractor quotes, ensure transparency, and navigate the renovation process with confidence.

Alternatively, you could pause bookings for a short period to complete any bigger changes without rushing.It really comes down to whether you’re prioritizing immediate income or taking the time to make it 100% yours.

If this job popped up out of the blue, your intent was not to move within the 1st year, so you may be ok.If you are planning on building a portfolio of homes, it is safest to stick in your home for 12 months to reduce the appearance of potential fraud. 

Liquidated damages can compensate the owner for lost rental income or extended financing costs.

In Italy your second house or even a duplex section the income is taxed higher.  

Here's a quick breakdown:Unforeseen Property Issues: Hidden damage, bad tenants, major repairs – these can eat into profits.Vacancy Woes: Empty units mean lost income, impacting cash flow.Market Downturns: Property values can drop, affecting your investment's performance. 

When it comes to analyzing properties, I’ve developed a specific checklist to make sure the home fits both resident needs and operational goals:Square Footage: Ideally, at least 2,000 sq. ft. to ensure enough living space for residents and staff.No Stairs or Pools: It reduces liability and keeps the home accessible for everyone (this is just my preference).Corner Lots: I love corner lots because they often provide extra parking and outdoor space—both of which are critical for families and visitors.