The double close or back to back closing is NOT illegal; it’s just darn hard to find a title insurer willing to do it.  

Again PMI offers the lower rate because its less risky and offers insurance to the bank.So when you sell your current home try and keep as much as possible and avoid an "All Cash" offer.

I didn’t go with his company to set up my life insurance policy.

You have taxes and insurance so that pulls another $100 per month- so you clear $600 per month. 

And STRs really help because you don't have the large dings that long term rentals have - i.e tenants damaging the property to where you have huge make ready costs (the str insurance covers that), no collections or evictions issues. 

The only way to answer that in general (whether house hacking in today's market is still a good option) or for a particular property, is to learn how to run the numbers and analyze a specific property to see whether it will be able to stand on its own as an investment when you move out someday.There are a lot of resources here on BP for doing that but I'd just say, make sure the assumptions you're putting into your spreadsheet or deal analyzer are realistic.Make sure the rents (especially for vacant units or pro-forma #s) are realistic by doing your own rent comps; make sure the mortgage rate is realistic by doing some research online and/or talking to some mortgage folks; make sure insurance #s are realistic by getting a couple of quotes for the # of units and zip code / area you're looking in; etc.I hope that helps, and good luck 😊

They do everything for you (payments, taxes, insurance coverage) - the website and app are easy and functional and you can vet your guests!

These companies do NOT have their own money they all tie into Large hedgefund or insurance company LOC's that can change on a whim and you know sheeet flows down hill.

Or if your not doing too much volume he can buy/partner in his personal name and get good liability insurance.

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).