However, the underlying financing stays in the name of the person I bought the property from. 

You will stay current on trends in the market, financing, etc. 4.

I've yet to stay with the same property manager that I've started out with in a new market, but I've eventually found the right one.

I am also thinking of doing the HELOC, use some of that for a down payment on a 3-4 unit and stay in my home.

Just touring the units will give you a good idea on how they treat the property and also gives you a chance to ask them if they like staying there or if there are any issues you should be aware of.

As you get more experience and your equity in the properties rise if they are doing value add deals then eventually and surprisingly quickly they could be leveraging into other deals, bankers gain more confidence in them, etc.

I agree with @Marie-therese Tai you really don’t want to force someone to stay just because of the lease.

We have also had issues where the occupant filed for BK and they were able to stay for 1 year and it cost us 10k in attorney fees to get them out.

In the beginning stay away from complexity-auctions, land contracts, FSBO etc.

We would looooove to house hack but seeing as it’s so expensive to buy in Brooklyn and we aren’t going to stay here long term, it doesn’t make sense for us.