. 😒 Essentially it is ok to trade this way with offshore accounts but, my understanding is it limits the usable brokerages as you may only use non-SEC regulated entities.

It is a gamble and I know the past few years were stable, but we are going into an unknown lending period.

You'll need to run the numbers, but since no one knows what the rate will be in 12-36months, you will always have to speculate (read that as gamble) on an ARM.

If you are asking specifically what appreciation impact will the NGA have on a specific neighborhood, I do not think anyone can answer...It's a bit of a gamble but it seems reasonable to think the NGA will bring some appreciation to neighboring homes.

You can do a cash-out refi on your house and blow the money gambling.

Or Offshore?)

In searching existing STRs, it is very clear this happens in practice, but I am not willing to buy a property and gamble that we can do an STR.

Not likely but it’s a gamble versus a scalable business approach.Develop an operating agreement.  

I use offshore assistants to manage everything, for pennies on the dollar.

I decided to gamble on appreciation and overbid on a duplex that will have good cash flow in Oak Park after losing another all cash deal (I bid all cash, over asking and was outbid by a buyer with similar terms with an offer “well above” mine on a different property in the same neighborhood.