Offer to be the guy that restores the old family property to it's former glory and all....Still it'll be hard to not look greedy because you do want to make money after all.....main thing to me is being super PATIENT.

The main reason I ask is because that is significantly below primary residence mortgage rates let alone any investment loans, if you can get rates like that I might need to make some changes on my end hahahTo answer your original question, assuming all else is equal long-term fixed rate debt is valuable. 

Lenders stopped allowing rent by the room due to modifications done to the property resulting in functional obsolescence and significant cost to cure in the event there was a default and they needed to foreclose on the home and resell it, given that the main buyer pool for single-family homes are primary occupants. 

My main question is whether it makes more sense to go the seller financing route and pay off the principal in 8–10 years or stick with a standard 30-year loan.My thinking is that the tax deductions from a mortgage wouldn’t outweigh the potential equity I could gain over those 8–10 years.

The main thing I see when coming across this is deferred maintenance.

Here is a video that runs down the basics - https://s-media.nyc.gov/agencies/specialenforcement/01-Legal...There is also a prohibited building list - https://www.nyc.gov/site/specialenforcement/registration-law...Here are some more info overall - https://www.nyc.gov/site/specialenforcement/registration-law..All of this makes STRs in the city pretty tough but it certainly not impossible.

Quote from @Garrett Brown: Hey @Josh Ball , this is basically what I do on the most successful properties I have ever had. www.cameronranchglamping.com It mainly depends on a few things.How close are you to a metro hub/ activities?

What states/cities make the most sense right now? 

@Madison SloanTo start house hacking, focus on saving for your down payment, researching target markets like Salt Lake City or North Idaho, and building a strong team of professionals, including an agent and lender.

You are taking over for someone who didn't care at all about the rules and you want the city to just be like, "yeah, this is fine"?