Im looking to transition from SFH and got into Multi-Family myself.

Selling your current home to transition into a new home and rental properties is a smart move.For selling your current home, conduct a thorough market analysis to price it competitively, enhance curb appeal, and consider minor improvements.

There is also a way to Refinance on the 5th month to close on the 6th month and transition it into a investment property.

But sellers typically prefer not to retain the buyer's contact information to facilitate a clean transition to the next transaction and avoid potential financial entanglements, It's essential for buyers to recognize that the original owner could reclaim ownership if the property was purchased from a title sale auction, with specific state regulations, such as a 2-year reclamation period in New York, Despite these factors, owner financing can benefit buyers by fostering a sense of connection with the seller.

However your situation becomes a trickier case study since these properties first served as your primary residence which could provide additional benefits form a tax perspective not available to an owner of investment real estate and nobody has a crystal ball and knows the property with certainty will transition into an investment property. 

What started out as an "accidental" BRRR transitioned into a buy and hold/ STR.

The rental market is ever shifting in region as we continue to transition out of the slower season.

As someone who just got licensed and transitioned into real estate, this is by far the most succinct explanation provided on this matter.

This was to ensure that I was able to supplement my income and allow for a smooth transition. 

It's great to hear about your interest in growing your portfolio and transitioning into full-time real estate investing adventures after your military career.