I looked at some properties in the Catskills last week that ultimately didn't fit the criteria.

or some other form of cash flow investment, I think renting fits our needs. 

Are there any apps or tools that you find particularly helpful?

You might find something that fits your needs.

Main problem is none of the home on market fit our needs/wants.

CT isn't cheap so if you plan on doing it there you are going to surprised at how poorly you do. maybe in the suburbs I'm not sure but as much as I know people call us from CT and everyone is rich and has lots of money and things are expensive out there. build to rent is a great model. we build 3 story walk up infill and keep it to the residential side. 3 units is the most units before it's commercial and you need engineering, etc. check comparable and things liek that. we came up with this design a year ago and we sold 10 if you want to talk further please DM me happy to connect. there are some great build to rent conferences. we went vertical not horizontal with it to save on build costs and design to fit on any infill lot. this fits on a 3500 square foot lot. most lots in our area are 30x120 or 30x150. in miami where I live now they are 50x100 or so. but any infill lot we can pretty much get this one on. there are some great build to rent conferences coming up too that if you like this topic I'd recommend attending I'm sure you'd learn a lot.  

Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.

If you’re open to looking across the state—from Jacksonville to Sarasota—you can definitely find some solid deals, but you’ve got to be strategic and focus on markets that fit your goals.

The best setups have:5-11 members (ideally 6-8).1 bedroom per member.1 bathroom for every 3 members.Look for properties with these specs:6-8 bedrooms.2-4 bathrooms.Ample parking (street or otherwise).Detached houses fit this formula beautifully, but other property types can work too.

He can't fit in the car.