Could this really work out?

I would really take the time to work out every number you could since you are GC, and go from there!

Yes, CT can be an expensive market but depending on where you work out of, it can be manageable.

But I would think it could/would certainly work out if the numbers look good.And yeah, I don't think you'd have to discount the space due to less SF, or not much anyway.

I agree with @Ashish Acharya if you're interested in reinvesting the proceeds into another investment property and your goal is to minimize your tax liability a 1031 would work out well for you.

You will need to work out a mutually-agreeable solution. 

Even on referrals a lot of contractors are hesitant to run around for investors new to an area until they trust that they will actually get work out of it.  

. 💰 At this point is a no brainer 🧠 and we know if it doesn’t work out or we don’t like doing it we can always revert to a traditional rental. 

Find out what rate rents are increasing and expenses are increasing in your area and use that in your underwriting, then work out each year of ownership. 5% rate in 5 years seems ambitious.

For many, if not most, this is likely to be after a workout, coffee, and around 10:00 AM in the morning on a weekend day or on a vacation day.