Since then, I have been able to leverage equity from those to finance non-owner-occupied deals.

(Unless you put down 20-25% and pay the higher NON-owner occupied interest rate .)So yes.

The one issue I think I’ll have on my hands is I prefer to house hack again in the same town (appreciation seems to be great along with rental amounts) but I’ll need to refinance my current house hack into a conventional which I doubt is at 20% equity yet since I don’t think I’ll have a valid excuse to have two owner occupied loans in the same town.

I'm actually a District Manager with Build 2 Rent here in Florida and we have off-market multifamily properties (both occupied and vacant) that you can purchase with a primary residence loan and interest rates in the low 4's.

But of the owner occupied loans I have completed, most borrowers were a mix of W2 and Self-employed.

So I've been doing my own taxes in Turbotax for 20 years now (I only own 2 rental properties but both were BRRRs), and I finally got stuck on something and went to a CPA 2 years ago, and he reviewed my past 5 years of returns and pointed out that I had made multiple mistakes (incorrectly categorizing repairs vs capex, calculating basis and therefore depreciation wrong, failing to realize that certain expenses for a home converted to a rental property start being deductible the day the property was placed in service vs actually occupied, the list goes on). 

I tend to take my property off market "hold" during slow times for some painting, other small updates and would never consider it as occupied.  

@Joe Scheffold any idea why isn't it occupied with students for this upcoming year?

Also with the new policy changes with CMHC high ratio mortgages first time home buyers will have a much tougher time buying their first home so the rental pool will increase leaving more people looking to rent.I currently hold two rentals one in which is an owner occupied rental which I purchased for 200k 7 years ago and it is worth around 275k today and this year I purchased a triplex as well for 250k and as is with no improvements this yields me an 8% return a year which I would say is quite low.

It's possible your loan officer is either unaware of the guidelines or his company has an overlay.As a lender who specializes in VA financing, I reach out to the VA Regional Loan Center of jurisdiction (based on what state the property is in) anytime I have a scenario like this, that way I have VA's position in writing to submit to my underwriters.Aside from the fact that both units are under lease for 10 more months, is there any other reason you could not occupy the home within 60 days?