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.

Although I am a Realtor and have access to the MLS and can see old listings, I have seen that Redfin has been pretty reliable as a #2 option.All in all, you want to compare properties with as many similar features as possible and be aware of the obvious outliers, with the main culprit being size difference (You really don't want to compare a 3000 sq. ft. house with 3 bedrooms to a 900 sq. ft. house with 3 bedrooms).

He was not fully aware of what his wife was doing when they signed the original lease, but I reviewed the lease and both he and his wife signed it.2.He stated that he was military and that there are stipulations other than receiving new orders to a new base that allow him to break the lease, he gave TDY as an example.

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.