Your development deal will look much like a flip in the eyes of the IRS since it is 6-9 months as well you'll have the short-term side of taxes, not the capital gains taxing on it.  

https://www.biggerpockets.com/blog/brrrr-loans-what-are-the-...Short-Term Rental Loans: What Are the Options and How Do DSCR Loans Stack Up?

Short answer: No.

.#8 I would consider your inspection cost a very cheap crash course in buying long distance investment properties. 

It will be a short term Airbnb rental.Have had success with two other Airbnb properties that I currently arbitrage in the local Pittsburgh area.Purchased the home far below market value with a probate sale.

Operating an LTR is quite different from managing a short-term rental , so I'd recommend focusing on mastering one strategy before expanding your portfolio.

     Just a reminder to everyone doing short term rentals to check with your county to see if you need to be paying a hotel occupancy tax.

Long story short if you are committed to house hacking the sky is the limits and there is endless possibility, it really comes down to your comfort level and where exactly you need to be in New Jersey.

Yes- I had the tenant sign a short term lease.

You will likely need to sit on the unit for a long time or reduce initial rent below the market for that unit to rent during the Winter. account for this by either offering a Winter special that will increase to market in the Spring or doing a short lease that ends in the Summer.