It mostly depends on what opportunities are put in front of you though.

It really depends on what a slight difference is. 

Then use the extra roommate rent income to pay down your mortgage and look to refi to a lower payment in the future (3-5 years) - so it cashflow when you move out.You could also choose the smaller unit and STR the other unit to generate more cash to pay down your mortgage and refi, so it cashflows when you move out.Bottom line: you'll have to get creative to solve your cashflow challenge!

I plan to continue to invest in a mix of both RE syndication and our own rental properties going forward depending on what makes the most sense and offers the best returns. 

If I have one property at or around market, I would choose to keep in the same or raise it a little.

You will have enough for a small downpayment on each option, depending on the area chosen in each case, and you won't have much of a cushion after closing costs. 

My dad and I (both with access to VA loans) are about to get into the multifam game and how we proceed is really going to depend on the true occupancy rules for the VA and our lender.

There are more listings to choose from now than any other time in nearly a decade.

It seems like each option could work depending on your long-term goals for those assets.

Start small with one property, choose a strategic location, stay transparent with lenders, and ensure tax compliance.