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?

Easy to purchase with DSCR loans for investors or Owner Occupied, FHA with low down-payment.

The only downside to my condo is that it is situated on the backside of the condominium it occupies and does not have an ocean view, however being aware of that I have dropped the price on significantly on the property. 

And under that definition, because there was no minimum time in the CZO for how long someone needed to occupy a structure to be considered "living" there, the court used literal dictionary definitions (standard practice in NH as can be seen in the similar case Working Stiff Partners v City of Portsmouth) to determine what constituted "living as a household" as it concerns STRs.The court explicity rejected the idea that this ruling should have larger implications for STRs around the state, and it certainly did not at all in any way prevent municipalities from regulating STRs.

Easy to purchase with DSCR loans for investors or Owner Occupied, FHA with low down-payment.

I have a duplex about to go up for sale in Fort Myers and currently have one for sale in Cape Coral that is owner occupied on side. 

I’ve owned one STR since 2005 that is occupied 240 nights a year and have incurred $1000 damage tops in 14 years.If you need an extra 300 bucks deposit to help you sleep at night, it could be costing you 20-30-40 times that in lost rents each year.  

i appreciate any valuable info about the loan product !!

For now, I’m planning to use an owner occupied loan. 

Planning to rent the 4/1.5 side by the room and house hack by living in 1 of the 4 bedrooms then planning to also rent the larger 1/1 side.Planning 5% down as owner occupied financing.