If it were me, I would like consider refinancing only 1 of the 2 properties now and considering the second later in 2025 or even early 2026 when rates potentially soften.

If that means renting out part of your residence, that's great for cash flow and experience. 

Congrats on orthodontic residency, though I know residency will be time consuming as well. 

I'm looking to purchase my first property with my fiancé (both 25) with the goal being to establish our primary residence together, as well as giving me the opportunity to add equity/value via rehab before moving on and converting the property into a rental within a year or so to kickstart an investment portfolio.An interesting lead that recently came up is my parent's neighbor's house.

Are you/your partner(s) foreign nationals or non-permanent resident aliens?

It's sometimes a little tougher to get one on an investment property vs. a primary residence but If you can get it I would strongly recommend looking into it. 

I was a southern CT resident for 15 years and own a rental property in Trumbull CT as well.

Unfortunately, this can make it unaffordable for some residents living in these parks. 

If you feel ambitious, you could try a BRRR strategy adding additional equity to the subject home and then taking equity out of it to pay off either the HELOC or if you decided to the refinance the primary residence. 

@Devan Praska I do not have a manual for my tenants but have created a manual for each of my properties in the event that something might happen to me and someone else would have to take over the management of them.