Once you devise a plan, execute it. 

I am considering purchasing a condo in Stamford, CT, to use as my personal residence, as I'll need to travel to CT frequently—about 50% of the time.

@Robert Brown personally I'd avoid Sosua, as it's a destination for sex tourism.There is also Santo Domingo, which attracts business travellers as well and the nearby beach city of Juan Dolio.

That's ~12% Cash on Cash return which seems pretty good/decent.My concerns are by doing this, it would reduce my rent price on the main house (most likely since they'd be sharing with other tenants on the property) and also I'm unclear whether adding an ADU would negatively affect the value of the property.Option 2Consider converting the property into a short/medium-term rental, specifically to travel nurses.

So there is no "intent" of transfer, just the RIGHT via execution of full terms and via completed execution of all terms which in such satisfies all encumbrances does title transfer. 

That's why most of the people never take off that sign up for Guru programs, because they don't give you actual steps which is how most people learn--you learn the blueprint and execute the steps.

Here in NW Florida, there's tons of options to house hack really nice homes if you rent by the bedroom or separate in law spaces through MTR to military or traveling nurses. 

We acclimated the flooring, but I suspect the existing tenant may keep the house at some very different temps (when she travels I suspect it's quite cool in the winter just warm enough to keep pipes form freezing, and very hot in the summer).  

They cater more to traveling professionals. 

The property cash flowed well and covered our expenses in 2021 and 2022 with short-term rentals and about 80-85% business use, but it did not rent as well in 2023 (oversaturated rental market, change in travel restrictions, weather etc...) and dropped to about 65% business use and a negative cash flow of about $15K.