Because of where interest rates are at—and how slow everything is moving—we basically made a "take it or leave it" deal.

Being owner occupied means getting the lowest interest rate, and a conventional or fha loan. 

Now, after doing this several times my success rate is around 1 out 5.   

The deal doesn't work as well with higher interest rates.

It's objectively rated as a great place to live, but obviously you need to be ok with Winter.

.- Low Interest Rates: Competitive interest rates make property ownership accessible, especially for those with stable income like service members.- Military Presence: With U.S. military bases across Germany, local banks are accustomed to assisting service members with financing.How to Qualify1.

First thing I'd do is check comps to get an idea of the demand and rates you can charge for your condo as a MTR.

Many of these lenders allowing 2nds behind them are more expensive capital (10's - 13's in our current market [high rates - but now showing signs of coming down]).

If he must attempt to get the low interest rates of 2021 on this deal, I suggest that he instead look for assumable loans.

I also wouldnt let your mom go into 2nd position on an investment property with any sort of restructuring; it doenst sound like she's in a position to risk being wiped out.Overall, though, if you want cashflow on the new property but cant achieve that after a refi into a market rate loan, it probably makes more sense to just flip it, pay off your heloc and your mom, and use the remaining capital for the next deal.