If you aren't going to live there, it isn't a "second home," it is an investment property. Your mortgage rate will be a little higher than for owner-occupied, but the interest, maintenance, depreciation, and fees will be tax deductable. See tax publications #527 and #946. You also might want to consult with a tax specialist at least the first year to make sure you have all the income and deductions in the right place. As someone pointed out, you will also have look for townhome and condo associations that allow rentals. They are very common in Florida, but I don't know about CT. As for finding good tenants, luck seems to be the biggest factor. Landlords who do complete credit checks and reference get burned from time to time. If you have enough cash flow, you might consider getting hiring a property manager to take care of everything, but filing taxes, for you.

Thank you for the suggestions. To answer the questions asked - we wouldn't need any additional cars as we already have two. Anywhere we move would still be within public transportation distance of the city as that is important to me. However it would be longer and probably on a commuter train with less frequency rather than a bus as I have now. About the slightly smaller home - any homes that are around even the ones that are smaller than ours are atleast $500k more so I am in the same place where I wonder what the value is in moving (which was my original question) The architect I had mentioned came by today and had some great suggestions that we could use to make the area we already have way more functional for us as a family. I am thinking about doing those changes (which she said would cost about ($30K) which involve breaking down a wall and adding a couple more windows and one additional door. The windows and door would require condo approval but everything else should be relatively easy to do! She did mention that it would be difficult to add another bedroom to the upstairs as there is value in keeping that big room as it is for now without dividing it up!

Congrats. What furnishings will you be bringing with you? This really cute condo is small enough that a room rug is unnecessary -- a room sized rug would even visually shrink and warm/heat the space. That doesn't mean you couldn't put a 3'x5' rug beneath a chair and ottoman. I grew up in a kitchen with walls and (metal) cabinets painted pale yellow, with only slightly darker yellow window trim and recently have been seriously considering repainting my own kitchen two shades of the same color ... perhaps blue; perhaps yellow. Perhaps you could use two shades of your own favorite color for your kitchen. Are you planning to leave the wallpaper trim tape atop the wall? If so, you might take that color into consideration as you choose your paint colors. Is that the back of a microwave I see at the peninsula? If you're not going to use that bar as a bar (wouldn't), consider removing it and perhaps adding a rectangle box shelf (with a back to it) the top of that pony wall so you'll have a shelf for your microwave and/or toaster oven without them sitting on your countertop. You'd probably have room to set S&P and sugar bowl and napkin holder on the countertop beneath the overhang of a box shelf and still be able to use the countertop space in front of that for meal prep. Instead of just a sideboard w/art beside the kitchen, consider a full 6' high china cabinet -- saving your kitchen cabinet space for other items. Having solid doors below give you storage for things you don't want to display; having glass doors above enables you to display some of your dishes. The open shelves in the middle enable you to place items there you need to access regularly such as decorative canisters. If your china cabinet and dining table/chairs are wood with a medium finish, that will visually warm your space. For end tables and bed side tables, consider 2drawer filing cabinets made of the same wood as your dining set. Not only will your "tables" do double duty as storage for documents you need to keep, the drawers are deep enough for purses and/or camera equipment and/or other hobby items. Some have a third shallow drawer above the two file drawers and some even have locks. https://www.google.com/search?q=two+drawer+wood+file+cabinets&source=lnms&tbm=isch&sa=X&ved=0ahUKEwjbupSi_7PaAhWLVN8KHfHRBxQQ_AUICygC&biw=1366&bih=650

You can get tile that looks just like wood planks and never worry about water damage again. I just put this in my home (bedrooms kitchen and great room) and it looks wonderful! People see it and cannot believe it is tile (and tile is much cheaper per square foot than most other flooring.) You will also save a ton not having to buy any special flooring cleaners. We also live at the beach so I don't have to worry about sand scratching up the floors either.