Most hit all the bullet points excepting:Spending $175 on renovation and adding square footage or unit count does NOT miraculously convert to valuation.

If I wholesaled I would get a license, I feel like they are losing a lot on commissions that they can convert to listings

The current option that we are looking at is buy, live in 1-2 months of the year, convert to MTR or STR for the other months (especially since we are flexible on our end). 

Yes, most lenders will require you to live in a primary residence before moving out, refinancing, or converting into a rental.

What if the city shuts the entire thing down until the basement is converted?

I’m in the process of converting one of the units into a short-term rental and could use some advice.I’m trying to figure out if it’s worth using a dynamic pricing tool to maximize revenue and whether I should invest in property management software to help manage bookings, communication, and other tasks.Any recommendations or insights from your experience would be greatly appreciated.

You could also sell it to rent to own, take a downpayment from it, and keep title open until the pay their part and re-assume title if they cannot convert.

But as of today, I am strongly considering converting it into a single-family rental because based on some Zillow comps I’ve seen I could get upwards of $8000.00 per month which is more than double my mortgage, taxes and operating expenses.

However, if you demonstrate that you're abusing FHA loans, such as getting a new loan after six months because you converted the property you just bought into a rental without a reasonable explanation, then you could have issues. 

This class will include hands-on deal analysis and a tour with a contractor to learn how to convert a home to the optimal PadSplit setup.